Sulfuric Acid → Ethyl (4-chlorophenyl)(hydroxy)acetate

HRID 1192369

Reaction equation

HRID 1192369 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.OS(O)(=O)=O.[C:18]1(C)C=CC=C[CH:19]=1>CCO>[CH2:18]([O:8][C:7](=[O:9])[CH:6]([C:5]1[CH:11]=[CH:12][C:2]([Cl:1])=[CH:3][CH:4]=1)[OH:10])[CH3:19]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 102994-Chloromandelic acid

Product 1

HCID 12373588Ethyl (4-chlorophenyl)(hydroxy)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloromandelic acid (12.3 g, 65.9 mmol) in toluene (50 mL), EtOH (16 mL), and concentrated H2SO4 (0.1 mL) was refluxed for 12 hours while removing water using a Dean-Stark trap. The mixture was concentrated in vacuo, diluted with DCM, and washed with dilute aqueous NaHCO3. The separated DCM layer was dried (MgSO4), filtered, and concentrated in vacuo to give (4-chlorophenyl)-hydroxy-acetic acid ethyl ester as a colorless oil (10.0 g) that crystallized upon standing.

Workup

  1. customwhile removing water using a Dean-Stark trap
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with DCM
  4. washwashed with dilute aqueous NaHCO3
  5. dry with materialThe separated DCM layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99f0d12bafec4c3f8ceb948efc975416
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Linked notes

Loading…