Sodium borohydride → Methyl 2-(4-hydroxymethylphenoxy)propionate

HRID 426433Notes

Reaction equation

HRID 426433 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18981016Methyl 2-(4-formylphenoxy)propanoate

Product 1

HCID 18759642Methyl 2-(4-hydroxymethylphenoxy)propionateYield 45.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

44 gm (0.211 mol) of methyl 2-(4-formyl-phenoxy)-propionate were dissolved in 500 ml of methanol, and 8 gm (0.211 mol) of sodium borohydride were added in small portions to the solution. The resulting mixture was stirred at room temperature for 30 minutes and then at 60° C. for 30 minutes. Thereafter, the reaction mixture was evaporated in vacuo to one-half its original volume, poured into water, neutralized with hydrochloric acid, and extracted with ether. The ethereal extract solution was washed, dried and evaporated, leaving 20 gm of methyl 2-(4-hydroxymethyl-phenoxy)-propionate as a colorless oil which was purified on a silicagel column with chloroform as the flow agent.

Workup

  1. waitat 60° C. for 30 minutes
  2. customThereafter, the reaction mixture was evaporated in vacuo to one-half its original volume
  3. additionpoured into water
  4. extractionextracted with ether
  5. extractionThe ethereal extract solution
  6. washwas washed
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-62d16ca9685148eaa8e7b96aac127038
Source dataset
uspto-grants-1979_10
Patent number
US04169720

Reaction notes

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