Phenacyl bromide → alpha-Hydroxyacetophenone

HRID 1937119Notes

Reaction equation

HRID 1937119 reaction equation
[CH:1]([O-:3])=O.[Na+].C(Br)[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7]>C(O)C>[CH2:1]([OH:3])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 2723810Sodium Formate

Product 1

HCID 68490alpha-Hydroxyacetophenone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

This procedure was adapted from the one developed by Pirkle and Simmons (Pirkle, W. H. and Simmons, K A., J. Org. Chem. 48:2520-2527 (1983)). 11.62 g (0.1706 moles) sodium formate was stirred in 50 ml ethanol for about 15 minutes. 5.31 g (26.7 mmol) phenacyl bromide was added to it and the mixture was refluxed under nitrogen at 105° C. for nearly 20 h. The reaction mixture was cooled and complete conversion of the starting material was confirmed by TLC. The solvent was evaporated and about 50 ml of boiling water was added and the solution was filtered hot. The filtrate was then cooled to precipitate out the alcohol. Yield 3.11 g (86%) from 5.31 g phenacyl bromide, white crystalline solid: mp 82-84° C. (lit. mp 84-85° C. (Pirkle, W. H. and Simmons, K A., J. Org. Chem. 48:2520-2527 (1983)); 1H NMR (CDCl3) δ6 3.49 (t, J=4.5), 4.87 (d, J=4.5), 7.44-7.65 (m, 3H), 7.91 (dd, J1=8, J21.3, 2H); 13C NMR (CDCl3) δ198.4, 134.3, 133.5, 129.0, 127.7, 65.5; EI-MS, m/z (rel. intensity) 136 (M+, 6), 105 (100), 77 (81), 52 (29).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe solvent was evaporated
  3. additionabout 50 ml of boiling water was added
  4. filtrationthe solution was filtered hot
  5. temperatureThe filtrate was then cooled
  6. customto precipitate out the alcohol

Sources & evidence

ORD record
ord-4a5cba1770ff4f6b9f2571ae65d06b39
Source dataset
uspto-grants-2002_05
Patent number
US06392089B1

Reaction notes

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