Water → 3,7-Dimethyl-4-[(1-ethoxyethoxy)]-6-octen-1-ol

HRID 1447536Notes

Reaction equation

HRID 1447536 reaction equation
C([O:4][CH2:5][CH2:6][CH:7]([CH3:20])[CH:8]([O:14][CH:15]([O:17][CH2:18][CH3:19])[CH3:16])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:20][CH:7]([CH:8]([O:14][CH:15]([O:17][CH2:18][CH3:19])[CH3:16])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH2:6][CH2:5][OH:4]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 233414488-Acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene

Product 1

HCID 233414523,7-Dimethyl-4-[(1-ethoxyethoxy)]-6-octen-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 8-acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene (0.5 mmole), saturated potassium carbonate solution (9 ml), water (6 ml) and methanol (100 ml) is stirred for 3 hours at room temperature. Most of the methanol is removed in vacuo and the residue is treated with ethyl acetate (500 ml) and water (200 ml). The organic phase is dried (Na2SO4) and evaporated in vacuo to give the crude product. This material is further purified by column chromatography on silica gel (25 g, 15% ethyl acetate in hexane) to give 3,7-dimethyl-4-[(1-ethoxyethoxy)]-6-octen-1-ol as a colorless oil.

Workup

  1. customMost of the methanol is removed in vacuo
  2. additionthe residue is treated with ethyl acetate (500 ml) and water (200 ml)
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give the crude product
  6. customThis material is further purified by column chromatography on silica gel (25 g, 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9a911e17e42c4f96ad0fbe06983b6d0d
Source dataset
uspto-grants-1979_12
Patent number
US04177194

Reaction notes

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