Hydrochloric Acid → [1-Oxo-2-(4-methoxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid

HRID 839679Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:22])[CH2:17][C:16]3[C:11](=[C:12]([Cl:20])[C:13]([Cl:19])=[C:14]([OH:18])[CH:15]=3)[C:10]2=[O:21])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]([O:33]CC)=[O:32].[OH-].[Na+].Cl>CN(C)C=O.O>[O:21]=[C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:18][CH2:30][C:31]([OH:33])=[O:32])=[C:13]([Cl:19])[C:12]=2[Cl:20])[CH2:17][C:9]1([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

A stirred mixture of 2-(4-methoxyphenyl)-2-methyl 5-hydroxy-6,7-dichloro-1-indanone (2.6 g., 0.0077 mole), potassium carbonate (2.14 g., 0.0154 mole) and ethyl bromoacetate (2.58 g., 0.0154 mole) in dimethylformamide (60 ml.) is warmed at 55°-60° C. for 2.5 hrs., then treated with water (60 ml.),-10N sodium hydroxide solution (3 ml., 0.03 mole) and heated at 100° C. for one hour. The reaction mixture is added slowly to crushed ice-water (600 ml.)-12N hydrochloric acid (20 ml.) to precipitate 1.69 g. of [1-oxo-2-(4-methoxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 173°-175° C. after crystallization from nitromethane.

Workup

temperatureis warmed at 55°-60° C. for 2.5 hrs
additionThe reaction mixture is added slowly
customto precipitate 1.69 g
customof [1-oxo-2-(4-methoxyphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 173°-175° C. after crystallization from nitromethane

Sources & evidence

ORD record: ord-ae36da0a217e42a6a4fc3a4d92faf5cd
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04096267

Reaction notes

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