Thionyl Chloride → 2,2-Dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carbonyl chloride

HRID 27049Notes

Reaction equation

HRID 27049 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:15]([OH:17])=O)[CH2:12][C:11]2([Cl:14])[Cl:13])=[CH:6][CH:5]=1)[CH3:2].S(Cl)([Cl:20])=O>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:15]([Cl:20])=[O:17])[CH2:12][C:11]2([Cl:14])[Cl:13])=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 135804022,2-Dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 130410812,2-Dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carbonyl chloride

Procedure

The 1-p-ethoxyphenyl-2,2-dichlorocyclopropane-1-carboxylic acid (1.38 g) was refluxed on a water bath with thionyl chloride (1.19 g) for 15 minutes. The excess thionyl chloride was then evaporated under vacuum (1 Torr.) and the residue of carbonyl chloride reacted without further purification with one of the alcohols (a), (b), (c) or (d). ##STR11##

Workup

  1. customThe excess thionyl chloride was then evaporated under vacuum (1 Torr.)
  2. customthe residue of carbonyl chloride reacted without further purification with one of the alcohols (a), (b), (c) or (d)

Sources & evidence

ORD record
ord-75f508af836148c784e52da5e9963009
Source dataset
uspto-grants-1980_09
Patent number
US04220591

Reaction notes

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