Hydrochloric Acid → HCID 86674042, compound

HRID 573968Notes

Reaction equation

HRID 573968 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:165]=[C:166]([O:187][CH2:188][CH2:189][CH2:190][CH2:191][CH2:192][CH2:193][CH2:194][CH2:195][CH2:196][CH2:197][CH2:198][CH2:199][CH2:200][CH2:201][CH2:202][CH2:203][CH2:204][CH3:205])[C:167]=1[O:168][CH2:169][CH2:170][CH2:171][CH2:172][CH2:173][CH2:174][CH2:175][CH2:176][CH2:177][CH2:178][CH2:179][CH2:180][CH2:181][CH2:182][CH2:183][CH2:184][CH2:185][CH3:186])[CH2:23][O:24][C:25]1[CH:26]=[C:27]([CH:32]=[C:33]([O:100][CH2:101][C:102]2[CH:107]=[C:106]([O:108][CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH2:116][CH2:117][CH2:118][CH2:119][CH2:120][CH2:121][CH2:122][CH2:123][CH2:124][CH2:125][CH3:126])[C:105]([O:127][CH2:128][CH2:129][CH2:130][CH2:131][CH2:132][CH2:133][CH2:134][CH2:135][CH2:136][CH2:137][CH2:138][CH2:139][CH2:140][CH2:141][CH2:142][CH2:143][CH2:144][CH3:145])=[C:104]([O:146][CH2:147][CH2:148][CH2:149][CH2:150][CH2:151][CH2:152][CH2:153][CH2:154][CH2:155][CH2:156][CH2:157][CH2:158][CH2:159][CH2:160][CH2:161][CH2:162][CH2:163][CH3:164])[CH:103]=2)[C:34]=1[O:35][CH2:36][C:37]1[CH:42]=[C:41]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[C:40]([O:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80])=[C:39]([O:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH3:99])[CH:38]=1)[C:28](OC)=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>COC1CCCC1>[CH2:188]([O:187][C:166]1[CH:165]=[C:22]([CH:21]=[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:167]=1[O:168][CH2:169][CH2:170][CH2:171][CH2:172][CH2:173][CH2:174][CH2:175][CH2:176][CH2:177][CH2:178][CH2:179][CH2:180][CH2:181][CH2:182][CH2:183][CH2:184][CH2:185][CH3:186])[CH2:23][O:24][C:25]1[CH:26]=[C:27]([CH:32]=[C:33]([O:100][CH2:101][C:102]2[CH:103]=[C:104]([O:146][CH2:147][CH2:148][CH2:149][CH2:150][CH2:151][CH2:152][CH2:153][CH2:154][CH2:155][CH2:156][CH2:157][CH2:158][CH2:159][CH2:160][CH2:161][CH2:162][CH2:163][CH3:164])[C:105]([O:127][CH2:128][CH2:129][CH2:130][CH2:131][CH2:132][CH2:133][CH2:134][CH2:135][CH2:136][CH2:137][CH2:138][CH2:139][CH2:140][CH2:141][CH2:142][CH2:143][CH2:144][CH3:145])=[C:106]([O:108][CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH2:116][CH2:117][CH2:118][CH2:119][CH2:120][CH2:121][CH2:122][CH2:123][CH2:124][CH2:125][CH3:126])[CH:107]=2)[C:34]=1[O:35][CH2:36][C:37]1[CH:38]=[C:39]([O:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH3:99])[C:40]([O:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80])=[C:41]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH:42]=1)[CH2:28][OH:29])[CH2:189][CH2:190][CH2:191][CH2:192][CH2:193][CH2:194][CH2:195][CH2:196][CH2:197][CH2:198][CH2:199][CH2:200][CH2:201][CH2:202][CH2:203][CH2:204][CH3:205]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydride2×HCID 86674043HCID 86674043, compound

Product 1

HCID 86674042HCID 86674042, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 138539Cyclopentyl methyl etherSolvent

Procedure

Methyl {3,4,5-tris[3,4,5-tris(octadecyloxy)benzyloxy]}benzoate (1.01 g, 350 μmol) was dissolved in dehydrating cyclopentyl methyl ether (20 mL) and, under ice-cooling, lithium aluminum hydride (31.8 mg, 840 μmol) was added, and the mixture was stirred at room temperature for 2 hr. After completion of the reaction, 0.1 mol/L aqueous hydrochloric acid was added dropwise to decompose unreacted lithium aluminum hydride and the mixture was washed with 1.0 mol/L aqueous hydrochloric acid. The organic layer was dried over sodium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure, methanol was added, and the precipitated solid was collected by filtration and dried under reduced pressure to give the title compound (940 mg, 94.6%) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. additionwas added dropwise
  3. washthe mixture was washed with 1.0 mol/L aqueous hydrochloric acid
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe obtained filtrate was concentrated under reduced pressure, methanol
  7. additionwas added
  8. filtrationthe precipitated solid was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-4354fa21de3d46378985e6adacde1051
Source dataset
uspto-grants-2015_05
Patent number
US09029528B2

Reaction notes

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