Phenacyl bromide → alpha-Hydroxyacetophenone

HRID 548191Notes

Reaction equation

HRID 548191 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C([O-])=[O:12].[Na+]>>[OH:12][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 2723810Sodium Formate

Product 1

HCID 68490alpha-Hydroxyacetophenone

Procedure

85% Ethanolic solution (1200 mL) of 2-bromo-1-phenylethanone (99.52 g, 500 mmol) and sodium formate (215.0 g, 3160 mol) was heated to reflux for 5 hours. After the solvent was evaporated in vacuo, water (1000 mL) was added to the residue and extraction with ethyl acetate was conducted. The organic layers were combined and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom in vacuo. Petroleum ether was added to the residual oily product to crystallize whereupon 2-hydroxy-1-phenylethanone (59.67 g, 88%) was produced. Mp. 86-89° C. 1H-NMR (DMSO-d6) δ: 4.81 (d, J=5.8 Hz, 2H), 5.07 (t, J=5.8 Hz, 1H), 7.50-7.55 (m, 2H), 7.63-7.67 (m, 1H), 7.92-7.95 (m, 2H)

Workup

  1. temperatureto reflux for 5 hours
  2. customAfter the solvent was evaporated in vacuo, water (1000 mL)
  3. additionwas added to the residue and extraction with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. additionPetroleum ether was added to the residual oily product
  7. customto crystallize whereupon 2-hydroxy-1-phenylethanone (59.67 g, 88%)
  8. customwas produced

Sources & evidence

ORD record
ord-ca1e257991b74f3192c9d0b11c13816c
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

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