Water → 3-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyloxy)-2-methoxypropanol

HRID 638516Notes

Reaction equation

HRID 638516 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:21])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:3][CH2:4]Br.[CH3:22][O:23][CH:24]([CH2:27][OH:28])[CH2:25][OH:26].[OH-].[K+].O>CS(C)=O.O1CCCC1>[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:21])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:3][CH2:4][O:26][CH2:25][CH:24]([O:23][CH3:22])[CH2:27][OH:28]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 111709312-Methoxypropane-1,3-diolHCID 545679811-Bromo-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

Product 1

HCID 541751673-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyloxy)-2-methoxypropanol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of 20 ml of dimethyl sulfoxide and 12 ml of tetrahydrofuran were dissolved 2.2 g of 3-(3,7, 11,15-tetramethyl-2,6,10,14-hexadecatetraenyl bromide and 2.3 g of 2-O-methylglycerin, and 2.0 g of powdered potassium hydroxide was added. The mixture was stirred for 2 hours, poured into cold water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by chromatography on a silica gel column to give 1.15 g of the above-identified compound as light-yellow liquid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-98ad48747a1c48728aea1fac0aa09968
Source dataset
uspto-grants-1985_12
Patent number
US04562005

Reaction notes

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