Water → 3-[[3-(Hexadecyloxy)-2-methoxypropoxy]methyl]benzenemethanol

HRID 1586681Notes

Reaction equation

HRID 1586681 reaction equation
[H-].[Na+].[C:3]1([CH2:11][OH:12])[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[CH:4]=1.[CH2:13]([O:29][CH2:30][CH:31]([O:34][CH3:35])[CH2:32]O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].O>CN(C)C=O>[CH2:13]([O:29][CH2:30][CH:31]([O:34][CH3:35])[CH2:32][O:10][CH2:9][C:5]1[CH:4]=[C:3]([CH2:11][OH:12])[CH:8]=[CH:7][CH:6]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 13801-O-hexadecyl-2-O-methylglycerolHCID 24758Sodium hydrideHCID 693741,3-Benzenedimethanol

Product 1

HCID 199395543-[[3-(Hexadecyloxy)-2-methoxypropoxy]methyl]benzenemethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 2.8 g of sodium hydride in 25 ml of dimethylformamide was added at 0° C. over 30 minutes a solution of 1,3-benzenedimethanol in 75 ml of dimethylformamide. After 30 minutes a solution of 3-(hexadecyloxy)-2-methoxy-1-propanol, 4-methyl benzene sulfonate in 25 ml of dimethylformamide was added over 30 minutes. After stirring 18 hours the mixture was poured into water and extracted with ethylacetate. The solution was dried and the product was purified by chromatography giving 4.7 g.

Workup

  1. extractionextracted with ethylacetate
  2. customThe solution was dried
  3. customthe product was purified by chromatography
  4. customgiving 4.7 g

Sources & evidence

ORD record
ord-b4aa7edb513a4aa1bd5f66672a77a89e
Source dataset
uspto-grants-1993_06
Patent number
US05215975

Reaction notes

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