Benzyl Bromide → 1-Phenyl-2,5,8,11,14,17,20,23,26,29-decaoxahentriacontan-31-ol

HRID 1162957Notes

Reaction equation

HRID 1162957 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([OH:41])[CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][OH:40].[Cl-].[NH4+]>C1COCC1>[CH2:3]([O:40][CH2:39][CH2:38][O:37][CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][OH:41])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 796893,6,9,12,15,18,21,24,27-Nonaoxanonacosane-1,29-diol

Product 1

HCID 595200441-Phenyl-2,5,8,11,14,17,20,23,26,29-decaoxahentriacontan-31-olYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (35 mg, 0.872 mmol) and benzyl bromide (52 μl, 0.436 mmol) were added to 5 mL of a solution of commercially available decaethylene glycol (200 mg, 0.436 mmol) in THF, and the mixture was stirred at room temperature for 16 hours. Aqueous saturated ammonium chloride was added to the mixture, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 168 mg of crude decaethylene glycol monobenzyl ether as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-356dfe0246ac401bbb57378242afe2bb
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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