Toluene → Benzoic acid, 2-fluoro-4-hydroxy-, 6-ethoxy-1-(trifluoromethyl)hexyl ester

HRID 1292579Notes

Reaction equation

HRID 1292579 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([O:13][CH:14]([C:23]([F:26])([F:25])[F:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH3:22])=[O:12])=[C:7]([F:27])[CH:6]=1)(=O)C.C1(C)C=CC=CC=1.CN>CO>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([O:13][CH:14]([C:23]([F:24])([F:25])[F:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH3:22])=[O:12])=[C:7]([F:27])[CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6329MethylamineHCID 11112008HCID 11112008, compound

Product 1

HCID 11013593Benzoic acid, 2-fluoro-4-hydroxy-, 6-ethoxy-1-(trifluoromethyl)hexyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reactor was charged with 1 g of 4-acetoxy-2-fluoro-1-(6-ethoxy-1-trifluoromethylhexyloxy-carbonyl)benzene (formula (1); X=F, Y=--CF3, Q=--CH3, m=1, p=5, n=2), 15 ml of toluene and 0.5 g of a methanol solution containing 40 wt% methylamine, and the mixture is stirred at room temperature for 15 minutes. After the reaction, the reaction mixture was washed with a 4 wt% hydrochloric acid aqueous solution and then with water to separate an organic layer from the solution. The organic layer was dried over anhydrous sodium sulfate, and then, the solvent is distilled off to give 4-hydroxy-2-fluoro-1-(6-ethoxy-1-trifluoromethylhexyloxy-carbonyl)benzene (formula (2); X=F, m=1, p=5, n=2). This product was dissolved in acetone and analyzed by gas chromatography to show no presence of methylacetamide (CH3CONHCH3).

Workup

  1. customAfter the reaction
  2. washthe reaction mixture was washed with a 4 wt% hydrochloric acid aqueous solution
  3. customwith water to separate an organic layer from the solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-6d073e4cea2c4c64be3094cffa15af34
Source dataset
uspto-grants-1998_05
Patent number
US05756816

Reaction notes

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