2-Chloroacetophenone → 2-Chloro-1-phenylethanol

HRID 989911Notes

Reaction equation

HRID 989911 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+]>CO>[Cl:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4]

Participants

4

Conditions

Temperature
0 °C

Procedure

2-Chloroacetophenone (5.0 g, 32 mmole) was dissolved in methanol (25 mL) and cooled to 0° C. Sodium borohydride (1.2 g, 32 mmole) was added and stirred at 0° C. for 30 minutes. The reaction mixture was neutralized by adding conc. HCI to pH 7.0 and evaporated to dryness. The residue was dissolved in ethanol (30 mL) and filtered, washed with ethanol. The ethanol was evaporated to dryness. The residue was dissolved in methylene chloride (20 mL) and dried over sodium sulfate. The methylene chloride solution was filtered and evaporated to give the desired product as an oil; yield 4.84 g (5.6%).

Workup

  1. additionby adding conc. HCI to pH 7.0
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in ethanol (30 mL)
  4. filtrationfiltered
  5. washwashed with ethanol
  6. customThe ethanol was evaporated to dryness
  7. dissolutionThe residue was dissolved in methylene chloride (20 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationThe methylene chloride solution was filtered
  10. customevaporated

Sources & evidence

ORD record
ord-335d42890264490b83d42f7ad0525a39
Source dataset
uspto-grants-2002_10
Patent number
US06458819B1

Reaction notes

Loading…