Water → 3-Benzyl-1,2-dihexadecylglycerol

HRID 1464230Notes

Reaction equation

HRID 1464230 reaction equation
[CH2:1]([CH:8]([CH:10]([CH2:12][OH:13])O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:14].[K+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[OH2:33].[C:34]1([CH3:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:40]([O:14][CH2:5][CH:6]([O:13][CH2:12][CH2:10][CH2:8][CH2:1][CH2:2][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:10][CH2:8][CH2:1][CH2:2][CH2:3][CH3:4])[CH2:7][O:33][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 82131-BromohexadecaneHCID 14797Potassium HydroxideHCID 2735483Benzylglycerol

Product 1

HCID 105798713-Benzyl-1,2-dihexadecylglycerol

Procedure

To a refluxing mixture of benzylglycerol (50 g, 0.27 mol) and KOH (40 g, 0.76 mol), which had been freshly powdered in an electric milling device, in toluene (500 mL) was added 1-bromohexadecane (252 g, 9.76 mol) over a period of one hour. The mixture was refluxed overnight, with Dean-Stark removal of water of reaction. The slurry was stripped of toluene on a rotary evaporator, then the residue was slurried in CHC13 and washed with water. The organic phase was dried (MgSO4) and stripped. Unreacted starting material was removed by Kugelrohr distillation (150°, 1 mm Hg). The pot residue was a yellow solid of sufficient purity for use in the next step.

Workup

  1. customThe slurry was stripped of toluene on a rotary evaporator
  2. washwashed with water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customwas removed by Kugelrohr distillation (150°, 1 mm Hg)

Sources & evidence

ORD record
ord-07f964a81d954222a0ef93b5da7ad283
Source dataset
uspto-grants-1994_04
Patent number
US05304325

Reaction notes

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