Methanol → 2-[1-(4-Chlorophenyl)cyclobutyl]-2,2-dimethoxyethanol

HRID 728291Notes

Reaction equation

HRID 728291 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](=[O:15])[CH2:13]Br)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:16][O-:17].[Na+].[Na].[OH2:20].[CH3:21]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([O:15][CH3:21])([O:17][CH3:16])[CH2:13][OH:20])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 887Methanol2×HCID 962WaterHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 219019212-Bromo-1-[1-(4-Chlorophenyl)cyclobutyl]ethanone

Product 1

HCID 198237812-[1-(4-Chlorophenyl)cyclobutyl]-2,2-dimethoxyethanol

Procedure

A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-2-bromoethanone (3 g) in methanol (10 ml) was added to sodium methoxide prepared by the reaction of sodium (0.46 g) and methanol (20 ml) and the mixture was stirred for two hours, and then poured into water. The aqueous mixture was extracted with ether and the extract dried and evaporated to give 2-[1-(4-chlorophenyl)cyclobutyl]-2,2-dimethoxyethanol (m.p. 73°-74° C.).

Workup

  1. extractionThe aqueous mixture was extracted with ether
  2. customthe extract dried
  3. customevaporated

Sources & evidence

ORD record
ord-0b60b2f174fe45f48ae928fc2ce6712d
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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