2-(3-Formylphenoxy)acetic acid → [3-(Hydroxymethyl)phenoxy]acetic acid

HRID 979542Notes

Reaction equation

HRID 979542 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([OH:10])=[O:9])=[O:2].[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 6018952-(3-Formylphenoxy)acetic acidHCID 4311764Sodium borohydride

Product 1

HCID 246028[3-(Hydroxymethyl)phenoxy]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3-formylphenoxyacetic acid (5.Og.) in ethanol (50 ml.) was added to a suspension of sodium borohydride (2.11 g.) in ethanol (100 ml.) with stirring. After 2 hours the reaction was quenched with acetic acid (20%, 50 ml.) and the bulk of the solvent was evaporated. Water (50 ml.) was added and the aqueous mixture was extracted with ethyl acetate (2×100 ml.). The combined extracts were washed with saturated brine (100 ml.), dried (MgSO4) and evaporated to give 3-(hydroxymethyl)phenoxyacetic acid (4.66 g.) as an off white solid, NMR: 4.5(2H,s), 4.65 (2H,s) and 6.6-7.4 (4H,m)ppm, which was used without further purification.

Workup

  1. customAfter 2 hours the reaction was quenched with acetic acid (20%, 50 ml.)
  2. customthe bulk of the solvent was evaporated
  3. additionWater (50 ml.) was added
  4. extractionthe aqueous mixture was extracted with ethyl acetate (2×100 ml.)
  5. washThe combined extracts were washed with saturated brine (100 ml.)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-d9cd199b1dd8416b9506870915b4f6b6
Source dataset
uspto-grants-1987_05
Patent number
US04668698

Reaction notes

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