Acetic Acid → HCID 13721957, compound

HRID 1413852Notes

Reaction equation

HRID 1413852 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[OH:13])=[O:5].C(O)(=O)C>CO>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]([OH:13])=[C:6]([CH:4]([OH:5])[CH3:3])[CH:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 740613-Chloro-6-hydroxyacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 13721957HCID 13721957, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.5 g) was added in small portions to a cooled solution of 5-chloro-2-hydroxyacetophenone (5 g) in methanol (50 ml). The solution was stirred at room temperature for 0.5 hr and was then poured into ice-water and acidified with dilute acetic acid. The product was extracted with ether, the ethereal solution was washed with water and then 5% aqueous sodium bicarbonate solution. The ethereal solution was dried (Na2SO4) and the solvent removed under reduced pressure. The colourless oil crystallised from hexane/ethyl acetate to give 4-chloro-2-(1-hydroxyethyl)phenol (4.8 g); m.p. 98° C.

Workup

  1. extractionThe product was extracted with ether
  2. washthe ethereal solution was washed with water
  3. dry with materialThe ethereal solution was dried (Na2SO4)
  4. customthe solvent removed under reduced pressure
  5. customThe colourless oil crystallised from hexane/ethyl acetate

Sources & evidence

ORD record
ord-433c71a595b14640b20f8c429ad54c41
Source dataset
uspto-grants-1981_02
Patent number
US04251546

Reaction notes

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