Hydrogen Bromide → 4-Hydroxyphenylacetone

HRID 1607862Notes

Reaction equation

HRID 1607862 reaction equation
Br.C[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1>O>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 312311-(p-Methoxyphenyl)-2-propanone

Product 1

HCID 70192744-Hydroxyphenylacetone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Hydrobromic acid (48%, 250 mL) was heated to approximately 120° C. Over a period of two minutes, a 9.85 g sample of 4-methoxyphenylacetone was added dropwise. After 15 minutes, the reaction mixture was chilled to 30° C. and diluted to 500 mL with distilled water. The resulting mixture was extracted twice with 250 mL portions of diethyl ether. The combined organic extracts were washed with brine, dried over magnesium sulfate, and the solvent was removed in vacuo. The resulting oil was purified immediately by column chromatography over silica gel, using 40% ethyl acetate and 60% hexane. Appropriate fractions were pooled and solvents removed in vacuo to yield a thick yellow oil.

Workup

  1. waitAfter 15 minutes
  2. extractionThe resulting mixture was extracted twice with 250 mL portions of diethyl ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe resulting oil was purified immediately by column chromatography over silica gel
  7. customsolvents removed in vacuo
  8. customto yield a thick yellow oil

Sources & evidence

ORD record
ord-9aeaced2d1ca46b59e002f28a23cbae6
Source dataset
uspto-grants-1989_09
Patent number
US04868132

Reaction notes

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