Dimethylformamide → 1-(3-Chloro-2-methyl-1-propenyl)-4-methylbenzene

HRID 29118Notes

Reaction equation

[CH3:1][C:2](=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[CH2:3]O.CN(C)C=O.S(Cl)([Cl:20])=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[Cl:20][CH2:3][C:2]([CH3:1])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 13.5 °C

Procedure

To a solution of 2-methyl-3-(4-methylphenyl)-2-propen-1-ol (750 g) in toluene (2367 ml) was added dimethylformamide (29.6 ml). To the solution was added dropwise thionyl chloride (431.1 ml) at 20° C. or below and the solution was stirred at 12 to 15° C. for 1.5 hr. Water was then added thereto under ice-cooling. The toluene layer was fractionated and a 10% aqueous solution of sodium carbonate was added thereto to adjust the pH to 5. The toluene layer was fractionated again, washed successively with 5% sodium hydrogencarbonate and 5% brine. The solvent was distilled off to give the title compound as an oil (776.8 g, yield 87.3%).

Workup

temperatureunder ice-cooling
washwashed successively with 5% sodium hydrogencarbonate and 5% brine
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-8ead58610936490782db289cb5170e76
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420070B2

Reaction notes

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