Chloroacetic Acid → 4-Carboxymethoxy-3-methylmandelic acid

HRID 1708256Notes

Reaction equation

HRID 1708256 reaction equation
Cl[CH2:2][C:3]([OH:5])=[O:4].[OH:6][C:7]1[CH:17]=[CH:16][C:10]([CH:11]([OH:15])[C:12]([OH:14])=[O:13])=[CH:9][C:8]=1[CH3:18].[OH-].[Na+].Cl>O>[C:3]([CH2:2][O:6][C:7]1[CH:17]=[CH:16][C:10]([CH:11]([OH:15])[C:12]([OH:14])=[O:13])=[CH:9][C:8]=1[CH3:18])([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 233614054-Hydroxy-3-methylmandelic acid

Product 1

HCID 189612624-Carboxymethoxy-3-methylmandelic acidYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4.7 g (0.05 mol) of chloroacetic acid is added to a solution of 9.11 g (0.05 mol) of 4-hydroxy-3-methylmandelic acid and 6.0 g (0.15 mol) of sodium hydroxide in 25 ml of water, and the mixture is then stirred at 80° C. for 3 hours. The reaction mixture is acidified with concentrated hydrochloric acid, cooled with ice/water, and the precipitated product is filtered, washed with water and dried in a high vacuum, giving 5.65 g (62%) of 4-carboxymethoxy-3-methylmandelic acid, melting point 95°-100° C.

Workup

  1. filtrationthe precipitated product is filtered
  2. washwashed with water
  3. customdried in a high vacuum

Sources & evidence

ORD record
ord-7ad85cd0400d4053a4f86fd9abec41dd
Source dataset
uspto-grants-1994_10
Patent number
US05356966

Reaction notes

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