Benzyl Bromide → 1-Hexyl-2-(2-(phenylmethoxy)-3-(triphenylmethoxy)propoxy)-4-tetradecylbenzene

HRID 34852Notes

Reaction equation

HRID 34852 reaction equation
[CH2:1]([C:7]1[CH:37]=[CH:36][C:35]([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][CH3:51])=[CH:34][C:8]=1[O:9][CH2:10][CH:11]([OH:33])[CH2:12][O:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[CH2:54](Br)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>CN(C)C=O>[CH2:1]([C:7]1[CH:37]=[CH:36][C:35]([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][CH3:51])=[CH:34][C:8]=1[O:9][CH2:10][CH:11]([O:33][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[CH2:12][O:13][C:14]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 150302691-(2-Hexyl-5-tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol

Product 1

HCID 150302701-Hexyl-2-(2-(phenylmethoxy)-3-(triphenylmethoxy)propoxy)-4-tetradecylbenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 13.8 g portion of 1-(2-hexyl-5-tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol in 40 ml of dimethylformamide was added dropwise to a suspension of 14.5 g of prewashed 50% sodium hydride in 40 ml of dimethylformamide and the mixture was stirred 15 minutes. A 4.45 g portion of benzyl bromide was added and the mixture was stirred an additional 3 hours. This mixture was quenched slowly with water and then extracted several times with ether. The ether extracts were combined, washed with water, brine, dried and evaporated giving 15 g of the desired compound.

Workup

  1. stirringthe mixture was stirred an additional 3 hours
  2. customThis mixture was quenched slowly with water
  3. extractionextracted several times with ether
  4. washwashed with water, brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-437be5a61c024861947fc77301620416
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Reaction notes

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