4-Hydroxybenzyl Alcohol → 170108-96-0

HRID 1518637Notes

Reaction equation

HRID 1518637 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18]C=C>CN(C)C=O>[C:10]([O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1)(=[O:13])[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 54514640170108-96-0Yield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

4-(Hydroxymethyl)phenol (620 mg, 5.0 mmol) was dissolved in N,N-dimethylformamide (25 ml) and potassium carbonate (1.38 g, 10.0 mmol) and 4-bromo-1-butene (1.08 g, 8.0 mmol) were added thereto. After stirring at 70° C. for 4 hours, the reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain [4-(2-propenoyloxy)phenyl]methanol (267 mg).

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-94695b419fc646338b6196916af62f96
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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