Hydrochloric Acid → 2-Hydroxy-3-(4-methylphenyl)propanoic acid

HRID 643234Notes

Reaction equation

HRID 643234 reaction equation
C[O:2][C:3](=[O:14])[CH:4](Cl)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1.C(=O)([O-])[O-:16].[Ca+2].[OH-].[Na+].Cl>O.O1CCOCC1>[OH:16][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[C:3]([OH:2])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10112Calcium CarbonateHCID 14798Sodium HydroxideHCID 143978892-Chloro-3-p-tolyl-propionic acid methyl ester

Product 1

HCID 576385742-Hydroxy-3-(4-methylphenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mechanically stirred suspension of 2-chloro-3-p-tolyl-propionic acid methyl ester (23 g, 0.1 mol), calcium carbonate (11 g, 0.1 mol), sodium hydroxide (5.5 g, 0.11 mol), 200 ml of dioxane and 300 ml of water is heated at reflux for 16 hours. After cooling to room temperature, 1.3 l of 2 N hydrochloric acid are added and the mixture is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate and evaporated to yield 2-hydroxy-3-p-tolyl-propionic acid, which is sufficiently pure to be used in the next step.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hours
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-b7a19091f7314ad5ac4ab33d5f1458fe
Source dataset
uspto-grants-2010_04
Patent number
US07700522B2

Reaction notes

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