Thionyl Chloride → 2-(4-(Chlorosulfonyl)-3,5-dimethylphenoxy)acetyl chloride

HRID 628154Notes

Reaction equation

HRID 628154 reaction equation
[Cl:1][S:2]([C:5]1[C:15]([CH3:16])=[CH:14][C:8]([O:9][CH2:10][C:11](O)=[O:12])=[CH:7][C:6]=1[CH3:17])(=[O:4])=[O:3].O=S(Cl)[Cl:20]>>[Cl:1][S:2]([C:5]1[C:15]([CH3:16])=[CH:14][C:8]([O:9][CH2:10][C:11]([Cl:20])=[O:12])=[CH:7][C:6]=1[CH3:17])(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 224793222-(4-(Chlorosulfonyl)-3,5-dimethylphenoxy)acetic acid

Product 1

HCID 867153652-(4-(Chlorosulfonyl)-3,5-dimethylphenoxy)acetyl chloride

Procedure

Referring to FIG. 37, 2-(4-(Chlorosulfonyl)-3,5-dimethylphenoxy)acetic acid (6 g, 21.6 mmol) was dissolved in SOCl2 (50 mL) and the reaction mixture was refluxed overnight. Proton NMR analysis on a sample from the reaction mixture exhibited the conversion went completion. Concentration of the mixture under reduced pressure gave product as a white solid (6.4 g, quantitative); 1H NMR (CDCl3, 300 MHz): δ 6.71 (s, 2H), 5.03 (s, 2H), 2.80 (s, 6H).

Workup

  1. temperaturethe reaction mixture was refluxed overnight

Sources & evidence

ORD record
ord-d7313183b4394e58a0c0a3b2e6eeb5a4
Source dataset
uspto-grants-2016_04
Patent number
US09309283B2

Reaction notes

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