Thionyl Chloride → 4-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoyl chloride

HRID 371020Notes

Reaction equation

HRID 371020 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:7]=1[O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][CH:14]([CH3:22])[C:15]([O:20][CH3:21])=[CH:16][C:17](O)=[O:18])=[CH:11][CH:10]=1>CCOCC>[Cl:5][C:6]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:7]=1[O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][CH:14]([CH3:22])[C:15]([O:20][CH3:21])=[CH:16][C:17]([Cl:3])=[O:18])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 538603484-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid

Product 1

HCID 570969654-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoyl chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride (20 ml.) is added to 4-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid (10 mm.) in anhydrous ether (10 ml.). The mixture is refluxed for a few hours. Then, ether and excess thionyl chloride is removed by vacuum to yield 4-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoyl chloride.

Workup

  1. temperatureThe mixture is refluxed for a few hours
  2. customThen, ether and excess thionyl chloride is removed by vacuum

Sources & evidence

ORD record
ord-f2df93c890cf47e388b4c46e0baa9a03
Source dataset
uspto-grants-1985_07
Patent number
US04529438

Reaction notes

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