1,2-Bis(chloromethyl)benzene → 1,2-Bis(chloromethyl)benzene

HRID 568180Notes

Reaction equation

[Cl:1][CH2:2][C:3]1[C:4]([CH2:9][Cl:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:11]([CH:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([O-:16])=[O:15])[CH3:12].[Na+]>CN(C)C=O>[Cl:1][CH2:2][C:3]1[C:4]([CH2:9][Cl:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:11]([CH:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([O:16][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][Cl:10])=[O:15])[CH3:12]

Participants

Conditions

Temperature: 120 °C

Procedure

To a glass-made three-necked flask (volume: 500 ml) with a condenser, 66.5 g (380 mmol) of α,α′-dichloro-o-xylene, 66.5 g of N,N-dimethylformamide and 63.2 g (380 mmol) of sodium 2-ethylhexanoate were added. After the mixture was heated and stirred at 120° C. for one hour, the reaction mixture was analyzed by the gas chromatography. The conversion of α,α′-dichloro-o-xylene, the yield of [2-(chloromethyl)phenyl]methyl 2-ethylhexanoate (based on sodium 2-ethylhexanoate), and the molar ratio of the [2-(chloromethyl)phenyl]methyl 2-ethylhexanoate produced to the diester compound as a by-product are shown in Table 1 below.

Workup

temperatureAfter the mixture was heated

Sources & evidence

ORD record: ord-f11737c251fa47d28a76d2b215d6f7d0
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180801B2

Reaction notes

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