Hydrochloric Acid → Benzenemethanol, 4-chloro-alpha-methyl-

HRID 1444616Notes

Reaction equation

HRID 1444616 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=[O:3].[BH4-].[Na+].Cl>CO>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([CH:2]([OH:3])[CH3:1])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7467P-ChloroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 18825Benzenemethanol, 4-chloro-alpha-methyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-Chloroacetophenone (15.5 g, 100 mmoles) was dissolved in 100 ml of methanol, and a solution of 5.67 g (150 mmoles) of sodium borohydride in 250 ml of methanol was slowly added to the solution. The resulting solution was stirred overnight at room temperature. To the reaction mixture was added 1 N hydrochloric acid, and the organic layer was extracted with diethyl ether. The organic layer was collected and dried over anhydrous sodium sulfate, followed by concentration to obtain 1-(4-chlorophenyl)ethanol [1H-NMR (300 MHz, CDCl3) 1.48 (d, J=6.3 Hz, 3H), 4.88 (q, J=6.6 Hz, 1H), 7.31 (s, 4H)] in a nearly pure form.

Workup

  1. extractionthe organic layer was extracted with diethyl ether
  2. customThe organic layer was collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-e3334d7ae10144ff932c2ba95b87bf54
Source dataset
uspto-grants-2010_02
Patent number
US07662899B2

Reaction notes

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