Water → 1H-Indene-1-carboxylic acid, 2,3-dihydro-

HRID 436165Notes

Reaction equation

HRID 436165 reaction equation
S(=O)(=O)(O)[OH:2].ClC1C=CC(C[C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][CH2:15][CH:16]3[C:21]#N)=CC=1.[OH2:25]>>[CH:16]1([C:21]([OH:2])=[O:25])[C:17]2[C:13](=[CH:12][CH:20]=[CH:19][CH:18]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 20310076HCID 20310076, compound

Product 1

HCID 857281H-Indene-1-carboxylic acid, 2,3-dihydro-

Procedure

To 60 % sulfuric acid is added 3.0 g. of 4-(p-chlorobenzyl)indan-1-carbonitrile and the mixture is refluxed in a current of nitrogen gas for 2 hours. After cooling, water is added and the mixture is extracted with ether. The ethereal solution is washed with water and extracted with a 5 % aqueous solution of potassium carbonate. The extract is rendered acidic with hydrochloric acid and the resultant precipitate is extracted with chloroform. The chloroform layer is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is crystallized from cyclohexane. The described procedure gives 4-p-chlorobenzyl)indan-1-carboxylic acid as crystals melting at 127°-129° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with ether
  3. washThe ethereal solution is washed with water
  4. extractionextracted with a 5 % aqueous solution of potassium carbonate
  5. extractionthe resultant precipitate is extracted with chloroform
  6. washThe chloroform layer is washed with water
  7. customdried
  8. distillationThe solvent is distilled off under reduced pressure
  9. customthe residue is crystallized from cyclohexane

Sources & evidence

ORD record
ord-cefc6ecb444443208bf7718e5837afc7
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

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