Hydrochloric Acid → HCID 88781849, compound

HRID 839675Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:21])[CH2:16][C:15]3[C:10](=[C:11]([Cl:19])[C:12]([Cl:18])=[C:13]([OH:17])[CH:14]=3)[C:9]2=[O:20])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C([O:30][C:31](=[O:34])[CH2:32]Br)C.[OH-].[Na+].Cl>CN(C)C=O.O>[OH2:17].[O:20]=[C:9]1[C:10]2[C:15](=[CH:14][C:13]([O:17][CH2:32][C:31]([OH:34])=[O:30])=[C:12]([Cl:18])[C:11]=2[Cl:19])[CH2:16][C:8]1([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:21].[O:20]=[C:9]1[C:10]2[C:15](=[CH:14][C:13]([O:17][CH2:32][C:31]([OH:34])=[O:30])=[C:12]([Cl:18])[C:11]=2[Cl:19])[CH2:16][C:8]1([CH3:21])[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred mixture of 2-(4-chlorophenyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (2.95 g., 0.00863 mole), potassium carbonate (2.26 g., 0.0163 mole) and ethylbromoacetate (2.72 g., 0.0163 mole) in dimethylformamide (50 ml.) is warmed at 55°-60° C. for 2 hours, then treated with water (50 ml.)-10N sodium hydroxide solution (2.5 ml., 0.025 mole) and heated at 80° C. for one hour. The reaction mixture is added slowly to water (500 ml.)-12N hydrochloric acid (10 ml.) to precipitate 1.37 g. of [1-oxo-2-(4-chlorophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid hemihydrate which melts at 141°-142° C. after crystallization from acetic acid:water, 1:1.

Workup

temperatureis warmed at 55°-60° C. for 2 hours
customto precipitate 1.37 g
customof [1-oxo-2-(4-chlorophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid hemihydrate which melts at 141°-142° C. after crystallization from acetic acid

Sources & evidence

ORD record: ord-348c9818526f441c8570291af229b6fa
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04096267

Reaction notes

Loading…