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

HRID 1650969Notes

Reaction equation

HRID 1650969 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](=[O:24])[CH2:13][CH2+]3CC4C(C)(C)C3(C)CC4)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:25][O-:26].[Na+].[Na].[OH2:29].[CH3:30]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]([O:24][CH3:30])([O:26][CH3:25])[CH2:13][OH:29])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

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

Procedure

A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-2-bormoethanone (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-fc8cf950b5294743a376a13b34ef4862
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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