4-Octyloxybenzoyl chloride → 4-Octyloxy-benzoic acid 4-[4-(11-bromo-undecyloxy)-phenyl]-cyclohexyl ester

HRID 2220004Notes

Reaction equation

HRID 2220004 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1.[CH2:27]([O:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:21][CH2:22][CH:23]([O:26][C:40](=[O:41])[C:39]3[CH:38]=[CH:37][C:36]([O:35][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:44][CH:43]=3)[CH2:24][CH2:25]2)=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 27602504-Octyloxybenzoyl chlorideHCID 179809754-[4-(11-Bromo-undecyloxy)-phenyl]-cyclohexanol

Product 1

HCID 693072994-Octyloxy-benzoic acid 4-[4-(11-bromo-undecyloxy)-phenyl]-cyclohexyl esterYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3 g (7.05 mmol) of 4-[4-(11-Bromo-undecyloxy)-phenyl]-cyclohexanol obtained in Step 2 and 2.02 g (7.52 mmol) of 4-Octyloxy-benzoyl chloride are dissolved in 100 mL of dry CH2Cl2. 0.95 g (7.52 mmol) of DMAP are added. The mixture is stirred at room temperature over night. The solvent is distilled off and then the resulting product is purified by column chromatography on silica gel using CH2Cl2 as eluent to give a pure product as a white solid (3.8 g, 82% yield).

Workup

  1. distillationThe solvent is distilled off
  2. customthe resulting product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ac16706ba91342c1a5e2c717707209ee
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

Loading…