Hydrochloric Acid → 3-(4-Chlorophenoxy)-2-hydroxypropanoic acid

HRID 544598

Reaction equation

HRID 544598 reaction equation
Cl[C:2]([CH3:7])([OH:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.Cl>[OH-].[Na+]>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:7][CH:2]([OH:6])[C:3]([OH:5])=[O:4])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 46844-ChlorophenolHCID 189546732-Chloro-2-hydroxypropanoic acid

Product 1

HCID 1011743-(4-Chlorophenoxy)-2-hydroxypropanoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1.8 g (14.7 mmoles) 3=chlorolactic acid and 3.4 g p-chlorophenol in 15 ml 3.3 N sodium hydroxide was stirred under reflux for two hours. The mixture was cooled to room temperature and acidified to pH=3, with concentrated hydrochloric acid. The resulting white crystals were filtered and dissolved in hot water and the hot solution was adjusted to pH=1 with concentrated sulfuric acid. Upon cooling the product, 3-(p-chlorophenoxy)-lactic acid was collected as clear crystals, 0.7 g, m.p. 135° to 136° C.; Edelson, et al., Biochem Pharmacol 18, 2331 (1969) reported m.p. 137° to 138° C.

Workup

  1. temperatureunder reflux for two hours
  2. filtrationThe resulting white crystals were filtered
  3. dissolutiondissolved in hot water
  4. temperatureUpon cooling the product, 3-(p-chlorophenoxy)-lactic acid
  5. customwas collected as clear crystals, 0.7 g, m.p. 135° to 136° C.

Sources & evidence

ORD record
ord-2afdab4c8ed74d5fb0fc86347e25934c
Source dataset
uspto-grants-1984_05
Patent number
US04451474

Linked notes

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