Sodium Hydroxide → 3,4-Xylyloxyacetic acid

HRID 1929626Notes

Reaction equation

HRID 1929626 reaction equation
C[O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([CH3:13])[CH:7]=1.[OH-].[Na+]>CO>[CH3:13][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[CH3:12])[O:5][CH2:4][C:3]([OH:14])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13381509HCID 13381509, compound

Product 1

HCID 833553,4-Xylyloxyacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3,4-dimethyl-phenoxy)-acetic acid methyl ester (7.399 g; 38.099 mmol) in MeOH (100 ml) was treated with aq. 1N NaOH (57 ml; 1.5 eq.), and the resulting mixture was further stirred at rt for 30 min. MeOH was then removed under reduced pressure, water (100 ml) was added followed by aq. 1N HCl (75 ml). Filtration of the precipitated solid, and drying under HV afforded (3,4-dimethyl-phenoxy)-acetic acid as a colorless solid (6.070 g; 88%). LC-MS: tR=0.81 min.; [M+H]+: no ionisation.

Workup

  1. customMeOH was then removed under reduced pressure, water (100 ml)
  2. additionwas added
  3. filtrationFiltration of the precipitated solid
  4. customdrying under HV

Sources & evidence

ORD record
ord-57cb984dd9894486ba8706a5b5c2169e
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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