Dimethylformamide → (+/-)-2-(2-Naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionyl chloride

HRID 973324Notes

Reaction equation

HRID 973324 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]([CH3:21])([C:17]([F:20])([F:19])[F:18])[C:14](O)=[O:15].S(Cl)([Cl:24])=O.CN(C)C=O>C1C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]([CH3:21])([C:17]([F:20])([F:19])[F:18])[C:14]([Cl:24])=[O:15]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 13384287(+/-)-2-(2-Naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionic acid

Product 1

HCID 20314457(+/-)-2-(2-Naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of (±)-2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionic acid (6.0 g.), thionyl chloride (7.5 ml.) and dimethylformamide (0.2 g.) in benzene (50 ml.) is heated under reflux for 10 minutes. The mixture is evaporated, benzene (20 ml.) is added and the evaporation repeated twice. Light petroleum (b.p. 40°-60° C., 150 ml.) and carton are added to the residue, and the solution is filtered and evaporated to give (±)-2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionyl chloride (5.35 g.) m.p. 39°-43° C.

Workup

  1. temperatureunder reflux for 10 minutes
  2. customThe mixture is evaporated
  3. additionbenzene (20 ml.) is added
  4. customthe evaporation
  5. additionLight petroleum (b.p. 40°-60° C., 150 ml.) and carton are added to the residue
  6. filtrationthe solution is filtered
  7. customevaporated

Sources & evidence

ORD record
ord-b7e036cfa088412792101cf37364bc61
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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