Water → 5-Chloro-1-(4-chlorophenoxy)-3,3-dimethylpentan-2-one

HRID 1153951Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.Cl[CH2:17][C:18](=[O:25])[C:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][Cl:22]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][C:18](=[O:25])[C:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][Cl:22])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

92.5 g (0.72 mol) of 4-chlorophenol and 99.4 g (0.72 mol) of potassium carbonate in 500 ml of toluene are heated under reflux for 2 hours, the water of reaction distilling off azeotropically. The mixture is cooled to 40° C., and 110 g (0.6 mol) of 1,5-dichloro-3,3-dimethyl-pentan-2-one in 300 ml of toluene are added. The reaction mixture is heated at 100° C. for 5 hours, and is then cooled and filtered off under suction from the inorganic residue. The filtrate is washed with dilute sodium hydroxide solution and water, dried over sodium sulphate and evaporated down. 136.3 g (82.6% of theory) of crude 1-(4-chlorophenoxy)-5-chloro-3,3-dimethyl-pentan-2-one are obtained, and this product is directly reacted further. ##STR32##

Workup

temperatureunder reflux for 2 hours
distillationdistilling off azeotropically
temperatureThe reaction mixture is heated at 100° C. for 5 hours
temperatureis then cooled
filtrationfiltered off under suction from the inorganic residue
washThe filtrate is washed with dilute sodium hydroxide solution and water
dry with materialdried over sodium sulphate
customevaporated down

Sources & evidence

ORD record: ord-c2e8b48eb26a4f579b60e78d7d2502bd
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04487776

Reaction notes

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