Methanol → Methyl (1-oxo-2-ethyl-2,6,7-trichloro-5-indanyloxy)acetate

HRID 1834679Notes

Reaction equation

[Cl-:1].[Li+].[O:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:10]([Cl:14])[C:11]=2[Cl:13])[CH2:6][CH:5]1[CH2:21][CH3:22].CO>CN(C)C=O>[O:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:10]([Cl:14])[C:11]=2[Cl:13])[CH2:6][C:5]1([CH2:21][CH3:22])[Cl:1]

Participants

Conditions

Temperature: 90 °C

Procedure

A stirred solution of cupric chloride dihydrate (4.25 g. and lithium chloride (0.765 g.) in dimethylformamide (10 ml.) is heated to 90° C. and to the mixture is added a solution of methyl (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)-acetate (4.7 g., 0.015 mole) in dimethylformamide. The reaction mixture is heated at 90° C. for two hours and poured onto ice. The product is extracted into ether (100 ml.), washed with water, dried over anhydrous sodium sulfate and the ether distilled at reduced pressure. There is thus obtained 2.5 g. of methyl (1-oxo-2-ethyl-2,6,7-trichloro-5-indanyloxy)acetate (53% yield) which melts at 111° C. after recrystallization from methanol.

Workup

additionpoured onto ice
extractionThe product is extracted into ether (100 ml.)
washwashed with water
dry with materialdried over anhydrous sodium sulfate
distillationthe ether distilled at reduced pressure

Sources & evidence

ORD record: ord-7112deea57d4481786a1666c9d2e820d
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04070539

Reaction notes

Loading…