Benzyl Bromide → 2-Ethyl-1(2-(phenylmethoxy)-3-(triphenylmethoxy)propoxy)-4-tetradecylbenzen

HRID 34842Notes

Reaction equation

HRID 34842 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:35]=[C:34]([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][CH3:49])[CH:33]=[CH:32][C:6]=1[O:7][CH2:8][CH:9]([OH:31])[CH2:10][O:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:4].[CH2:50](Br)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN(C)C=O>[CH2:3]([C:5]1[CH:35]=[C:34]([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][CH3:49])[CH:33]=[CH:32][C:6]=1[O:7][CH2:8][CH:9]([O:31][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:10][O:11][C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH3:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 150302641-(2-Ethyl-4-tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol

Product 1

HCID 150302652-Ethyl-1(2-(phenylmethoxy)-3-(triphenylmethoxy)propoxy)-4-tetradecylbenzenYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 2.016 g of prewashed sodium hydride in 125 ml of dimethylformamide was added dropwise a solution of 17.75 g of 1-(2-ethyl-4-tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol in 125 ml of dimethylformamide. This mixture was stirred 15 minutes, then 7.198 g of benzyl bromide was added and stirring was continued for an additional 3 hours. The reaction mixture was quenched slowly with water and then extracted several times with ether. The ether extracts were combined, washed with water, dried and the solvent evaporated, giving 19.9 g of the desired compound.

Workup

  1. stirringstirring
  2. waitwas continued for an additional 3 hours
  3. customThe reaction mixture was quenched slowly with water
  4. extractionextracted several times with ether
  5. washwashed with water
  6. customdried
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-4f645a6c7e86425b8f105e780f15a770
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Reaction notes

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