Toluene → 2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl chloride

HRID 335404Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:16])[C:13](O)=[O:14])[CH3:2].C1(C)C=CC=CC=1.S(Cl)([Cl:26])=O>CN(C)C=O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:16])[C:13]([Cl:26])=[O:14])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 50 ml volume four-necked flask, 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetic acid (8-a) (0.94 g), toluene (anhydrous) (3.0 ml) and dimethylformamide (anhydrous) (0.2 ml) were added under a nitrogen atmosphere and the internal temperature was raised to about 50° C. Thionyl chloride (0.45 ml) was added thereto and the resulting mixture was stirred at 50° C. for 2 hours. The mixture was concentrated under reduced pressure, and azeotropically distilled with toluene to give 0.96 g of 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl chloride (6-a).

Workup

concentrationThe mixture was concentrated under reduced pressure
distillationazeotropically distilled with toluene

Sources & evidence

ORD record: ord-22938ab90e7948e7b7b00d2683a6132f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884010B2

Reaction notes

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