Chloroacetic Acid → (2-Hydroxymethyl-phenoxy)-acetic acid

HRID 2073533Notes

Reaction equation

HRID 2073533 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].Cl[CH2:11][C:12]([OH:14])=[O:13].[OH-].[Na+].Cl>O>[C:12]([CH2:11][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 5146Salicyl AlcoholHCID 14798Sodium Hydroxide

Product 1

HCID 298778(2-Hydroxymethyl-phenoxy)-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2-hydroxybenzyl alcohol (0.5 mol), α-chloroacetic acid (0.5 mol) and solid sodium hydroxide (1.0 mol) in water (1L) is heated at reflux for 6 h. After this time the solution is cooled to ambient temperature and acidified to pH 4 with a 10% solution of hydrogen chloride in water. The product crystalizes from the acidified solution and is isolated and dried by filtration to give 2-Carboxymethoxybenzylalcohol which is used directly in the next step.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 h
  3. customThe product crystalizes from the acidified solution
  4. customis isolated
  5. customdried by filtration

Sources & evidence

ORD record
ord-3f12139839f34a16820fc18fdd2a6402
Source dataset
uspto-grants-1990_04
Patent number
US04918081

Reaction notes

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