2-(3,4,5-Tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenone → 9-(4-Chlorophenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenol

HRID 573036Notes

Reaction equation

HRID 573036 reaction equation
[CH2:1]([O:19][CH:20]1[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O: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][CH2:61][CH2:62][CH3:63])[CH2:23][CH:22]([CH2:64][O:65][C:66]2[CH:78]=[CH:77][C:76]3[C:75]4[C:70](=[CH:71][CH:72]=[CH:73][CH:74]=4)[C:69](=[O:79])[C:68]=3[CH:67]=2)[CH2:21]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].[Cl:80][C:81]1[CH:86]=[CH:85][C:84]([Mg]Br)=[CH:83][CH:82]=1>C1COCC1>[Cl:80][C:81]1[CH:86]=[CH:85][C:84]([C:69]2([OH:79])[C:68]3[CH:67]=[C:66]([O:65][CH2:64][CH:22]4[CH2:21][CH: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])[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O: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][CH2:61][CH2:62][CH3:63])[CH2:23]4)[CH:78]=[CH:77][C:76]=3[C:75]3[C:70]2=[CH:71][CH:72]=[CH:73][CH:74]=3)=[CH:83][CH:82]=1

Participants

4

Reactant 2

HCID 594992172-(3,4,5-Tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenoneHCID 178478191HCID 178478191, compound

Product 1

HCID 469266539-(4-Chlorophenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenolYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

2-(3,4,5-Tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenone (61.6 mg, 56.1 μmol) was dissolved in dehydrated THF (3 mL), 4-chlorophenyl-magnesium bromide (200 μmol) was added, and the mixture was stirred at 40° C. for 3 hours. After evaporation of the solvent, 0.5N hydrochloric acid (6 mL) was added to the residue to allow crystallization. The crystals were collected by filtration, washed well with hydrochloric acid, water and methanol in this order to give 9-(4-chloro-phenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenol (64.1 mg, 53.0 μmol, 94%).

Workup

  1. customAfter evaporation of the solvent, 0.5N hydrochloric acid (6 mL)
  2. additionwas added to the residue
  3. customcrystallization
  4. filtrationThe crystals were collected by filtration
  5. washwashed well with hydrochloric acid, water and methanol in this order

Sources & evidence

ORD record
ord-2d594b7d3ae940afa95c238343af3561
Source dataset
uspto-grants-2015_05
Patent number
US09029504B2

Reaction notes

Loading…