Diisopropyl Ether → 4-(3,5-Dichloro-4-methylphenyl)-4-oxobut-2-enoic acid

HRID 746269Notes

Reaction equation

C([O:4][C:5](=[O:7])[CH3:6])(=O)C.O.C(O)(=O)C=O.[CH3:14][C:15]1[C:20]([Cl:21])=[CH:19][C:18]([C:22]([CH3:24])=[O:23])=[CH:17][C:16]=1[Cl:25].C(OC(C)C)(C)C>S(=O)(=O)(O)O.C(O)(=O)C>[Cl:21][C:20]1[CH:19]=[C:18]([C:22](=[O:23])[CH:24]=[CH:6][C:5]([OH:4])=[O:7])[CH:17]=[C:16]([Cl:25])[C:15]=1[CH3:14]

Participants

Conditions

Temperature: 60 °C

Procedure

10.2 g (0.1 mole) of acetic anhydride were added to 9.3 g (0.1 mole) of glyoxylic acid monohydrate and the mixture was heated, with stirring, on an oil bath at 60° C. for 10 minutes to obtain a homogeneous solution. To this solution were added, in turn, 20.3 g (0.1 mole) of 3,5-dichloro-4-methylacetophenone, prepared as described in step (a) above, 28.8 g of acetic acid and a catalytic amount (300 mg) of concentrated sulphuric acid, whilst ice-cooling. The mixture was then heated, with stirring, on an oil bath at 105°-110° C. for 2 hours, after which it was cooled and 100 ml of diisopropyl ether were added. The mixture was stirred and the resulting crystals were collected by filtration and washed first with water and then with a small amount of diisopropyl ether, after which they were dried to give 20.8 g (yield 80.3%) of the desired 4-(3,5-dichloro-4-methylphenyl)-4-oxo-2-butenoic acid, melting at 206°-216° C.

Workup

temperaturethe mixture was heated
customto obtain a homogeneous solution
customprepared
temperatureThe mixture was then heated
stirringwith stirring, on an oil bath at 105°-110° C. for 2 hours
temperatureafter which it was cooled
stirringThe mixture was stirred
filtrationthe resulting crystals were collected by filtration
washwashed first with water
dry with materialwith a small amount of diisopropyl ether, after which they were dried

Sources & evidence

ORD record: ord-d3b7260e801f42c58fc0bfd7af3da17e
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04603201

Reaction notes

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