Acetone → 4-(4-Methoxyphenyl)butane-1,2-diol

HRID 1706893Notes

Reaction equation

HRID 1706893 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]2[CH2:13][O:12]2)=[CH:5][CH:4]=1.S(=O)(=O)(O)[OH:15].CC(=O)C.C(=O)(O)[O-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH:11]([OH:15])[CH2:13][OH:12])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 1513402-[2-(4-Methoxyphenyl)ethyl]oxiraneHCID 516892Sodium Bicarbonate

Product 1

HCID 124981434-(4-Methoxyphenyl)butane-1,2-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 12 parts of 2-[2-(4-methoxyphenyl)-ethyl]oxirane in 1.8 parts of sulfuric acid and 160 parts of 2-propanone are added 100 parts of water. The whole is stirred for 2 days at room temperature. The reaction mixture is stirred with a sodium bicarbonate solution and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated, yielding 1-[2-(4-methoxyphenyl)ethyl]-1,2-ethanediol as a residue.

Workup

  1. extractionthe product is extracted with trichloromethane
  2. customThe extract is dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-d9ead46dbb97413392dd3d21a7dc2c03
Source dataset
uspto-grants-1980_06
Patent number
US04209447

Reaction notes

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