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

HRID 35950

Reaction equation

HRID 35950 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)-2methoxy-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-b803c018fdff491c8fff6b3c2b716dd8
Source dataset
uspto-grants-1995_05
Patent number
US05411983

Linked notes

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