Toluene → HCID 86668173, compound

HRID 385107Notes

Reaction equation

HRID 385107 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[O:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.S(Cl)([Cl:33])=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:12]([C:13]([Cl:33])=[O:14])=[CH:11][C:10]=1[O:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 68109007HCID 68109007, compound

Product 1

HCID 86668173HCID 86668173, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 4-benzyloxy-3-methoxy-5-trifluoromethylbenzoic acid (601 mg), toluene (6 mL), N,N-dimethylformamide (1 droplet) and thionyl chloride (0.16 mL) were added, and then the mixture was stirred at 60° C. for 16 hours. The solvent was distilled off under reduced pressure and then azeotroped with toluene to obtain the title compound (657 mg) as a yellow oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-084cdea924c04321a8411b2b9e7309d5
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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