4-Hydroxybenzyl Alcohol → HCID 57655910, compound

HRID 911444Notes

Reaction equation

HRID 911444 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1.Br[CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].O>C(O)C>[OH:13][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([O:7][CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 21642Bromopinacolone

Product 1

HCID 57655910HCID 57655910, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Mix potassium carbonate (2.764 g, 20 mmol), 4-hydroxy-benzyl alcohol (1.49 g, 12 mmol) in absolute ethanol (100 mL), add 1-bromopinacolone (1.791 g, 10 mmol) dropwise. Heat the mixture under reflux for 12 h. Add water to dissolve the solid, and remove most of the ethanol in vacuo. Extract the mixture with EtOAc three times. Combine the organic layers, wash with brine, dry over Na2SO4, filter and concentrate. Purify the residue by chromatography on silica gel eluting with EtOAc:hexane (1:2) to provide the desired intermediate as a colorless oil (1.08 g, 48%). MS (ES+) m/z: 205 M+H−H2O)+.

Workup

  1. temperatureHeat the mixture
  2. temperatureunder reflux for 12 h
  3. customremove most of the ethanol in vacuo
  4. extractionExtract the mixture with EtOAc three times
  5. washCombine the organic layers, wash with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the residue by chromatography on silica gel eluting with EtOAc:hexane (1:2)

Sources & evidence

ORD record
ord-316991c75da943a7851f692e3c9629c2
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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