Acetone → HCID 66917027, compound

HRID 882924Notes

Reaction equation

HRID 882924 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-:13].[K+].[K+].[CH3:18][C:19]([CH3:21])=[O:20]>>[OH:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:18][C@@H:19]([OH:20])[CH2:21][OH:13])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 824523-(4-Hydroxyphenyl)propanol

Product 1

HCID 66917027HCID 66917027, compound

Procedure

To a solution of 3-(4-hydroxyphenyl)-1-propanol (15.0 g, 99 mmol) in acetone (300 mL) is added S-(−)-glycidol (10.0 g, 105 mmol) and potassium carbonate (20.0 g, 145 mmol) and the reaction mixture is heated at reflux for 24 h. The resulting mixture is allowed to cool to RT, filtered and the filtrate is concentrated in vacuo. Purification by column chromatography (SiO2, 0-4% MeOH in DCM) affords the product as a white solid. [M+H]+ 227.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 24 h
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customPurification by column chromatography (SiO2, 0-4% MeOH in DCM)

Sources & evidence

ORD record
ord-b4196ff795f34921a613db8f07d101fc
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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