Water → 2-[4-(2-Methylpropenyl)phenyl]propionic Acid

HRID 1902373Notes

Reaction equation

HRID 1902373 reaction equation
[OH2:1].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[OH2:13]>ClC1C=CC=CC=1Cl>[CH3:3][C:2]([CH3:7])=[CH:12][C:2]1[CH:7]=[CH:6][C:5]([CH:5]([CH3:6])[C:4]([OH:13])=[O:1])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 1563562-[4-(2-Methylpropenyl)phenyl]propionic Acid

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Procedure

A solution of p-toluenesulphonic acid monohydrate (8.4 g) in o-dichlorobenzene (60 ml) was heated at 110° to 120° and treated dropwise with a previously prepared solution of 2-[4-(1-hydroxy-2-dimethylethyl)phenyl]propionic acid (9 g) in o-dichlorobenzene (40 ml) over a period of 20 minutes at the same temperature. The reaction mixture was rapidly cooled to room temperature, poured into water and extracted several times with ether. The combined ethereal extracts were washed with water and then treated with a 5% solution of NaOH. The separated aqueous phase was acidified with a 10% solution of hydrochloric acid and extracted again with ether and the organic phase was separated.

Workup

  1. extractionextracted several times with ether
  2. washThe combined ethereal extracts were washed with water
  3. additiontreated with a 5% solution of NaOH
  4. extractionextracted again with ether
  5. customthe organic phase was separated

Sources & evidence

ORD record
ord-3d4b17e10c944e3aa7fd343a02c98c32
Source dataset
uspto-grants-1982_12
Patent number
US04362891

Reaction notes

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