Hydrochloric Acid → 2,3,4-Tris(octadecyloxy)benzhydryl alcohol

HRID 573966Notes

Reaction equation

HRID 573966 reaction equation
[CH2:1]([O:19][C:20]1[C:33]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[C:32]([O:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])[CH:31]=[CH:30][C:21]=1[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23])[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].[BH4-].[Na+].Cl>C(Cl)(Cl)Cl.CO>[CH2:1]([O:19][C:20]1[C:33]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[C:32]([O:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])[CH:31]=[CH:30][C:21]=1[CH:22]([OH:23])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride2×HCID 595103512,3,4-Trioctadecanoxybenzophenone

Product 1

HCID 469360472,3,4-Tris(octadecyloxy)benzhydryl alcoholYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
45 °C

Procedure

2,3,4-Tris(octadecyloxy)benzophenone (3.00 g, 3.04 mmol) was dissolved in a mixed solvent of chloroform (30 mL) and methanol (10 mL), sodium borohydride (360 mg, 9.51 mmol) was added, and the mixture was stirred at 45° C. for 2 hr. After completion of the reaction, 0.1 mol/L aqueous hydrochloric acid was added dropwise to decompose unreacted sodium borohydride and the mixture was washed with 1.0 mol/L aqueous hydrochloric acid. The organic layer was dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. Methanol was added to the concentrated solution, and the precipitated solid was collected by filtration and dried under reduced pressure to give the title compound (2.98 g, 99.0%) as a white solid.

Workup

  1. additionwas added
  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 filtrate was concentrated under reduced pressure
  7. additionMethanol was added to the concentrated solution
  8. filtrationthe precipitated solid was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-904ad277d0ce49d382b1dcbb8dc0acc7
Source dataset
uspto-grants-2015_05
Patent number
US09029528B2

Reaction notes

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