Sulfuric Acid → Methyl 2-(4-chlorophenyl)-2-hydroxyacetate

HRID 2112295Notes

Reaction equation

HRID 2112295 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:18](=O)([O-])[O-].[Na+].[Na+].C(OCC)C.CCCCCC>CO.O>[CH3:18][O:10][C:9](=[O:11])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[OH:12]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 102994-Chloromandelic acidHCID 10340Sodium CarbonateHCID 21584099Diethylether hexane

Product 1

HCID 13794067Methyl 2-(4-chlorophenyl)-2-hydroxyacetateYield 84.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(4-Chlorophenyl)-2-hydroxyacetic acid (40 g; 0.2 mol) is dissolved in 100 ml of methanol and stirred at +20° C. At this temperature 5 ml of concentrated sulfuric acid are added dropwise. After the addition is complete the reaction mixture is heated up to +45° C. and stirred for further 30 minutes. Then the reaction mixture is poured into a cooled (0° C.) solution of sodium carbonate (42 g; 0.4 mol) in 300 ml of water. The product is extracted with toluene (3×50 ml) washed with brine (3×50 ml) dried (Na2SO4) and evaporated. After crystallization from diethylether/hexane (10 g/80 g) 2-(4-chlorophenyl)-2-hydroxyacetic acid methylester (34 g; 84% yield) is obtained as a colorless solid. M.p. 54-55° C.

Workup

  1. additionAfter the addition
  2. temperatureis heated up to +45° C.
  3. stirringstirred for further 30 minutes
  4. additionThen the reaction mixture is poured into
  5. extractionThe product is extracted with toluene (3×50 ml)
  6. washwashed with brine (3×50 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-f5c0d410ae3f4d8cbf3b2398534f8689
Source dataset
uspto-grants-2009_04
Patent number
US07521579B2

Reaction notes

Loading…