Thionyl Chloride → 2,6-Diethyl-4-methylbenzyl chloride

HRID 1890228Notes

Reaction equation

HRID 1890228 reaction equation
[CH2:1]([C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH2:5]O)[CH3:2].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH2:5][Cl:16])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 667075402,6-Diethyl-4-methylbenzyl alcohol

Product 1

HCID 667076972,6-Diethyl-4-methylbenzyl chlorideYield 158.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 138.41 g of 2,6-diethyl-4-methylbenzyl alcohol and 820 g of toluene was added dropwise 60.96 g of thionyl chloride at 25° C. over 4.5 hours. The resultant mixture was stirred for 15 hours. The reaction mixture was concentrated to obtain 159.58 g of 2,6-diethyl-4-methylbenzyl chloride (GC-area: 71%) as a brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-8a9772cead8647128b59ef23caf641f5
Source dataset
uspto-grants-2013_08
Patent number
US08507410B2

Reaction notes

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