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

HRID 1292581Notes

Reaction equation

HRID 1292581 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.C(O)C.C(N)C1C=CC=CC=1>O>[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 702EthanolHCID 7504BenzylamineHCID 11112008HCID 11112008, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reactor was charged with 1 g of 4-acetoxy-2-fluoro-1-(6-ethoxy-1-trifluoromethylhexyloxycarbonyl)-benzene, 15 ml of ethanol and 0.6 g of benzylamine, and the mixture was stirred at room temperature for 5 hours. After the reaction, the reaction mixture solution was poured into water and subjected to extraction with dichloromethane. An organic layer was consecutively washed with a hydrochloric acid aqueous solution and with water, and dried over anhydrous sodium sulfate. The solvent was removed to give a crude 4-hydroxy-2-fluoro-1-(6-ethoxy-1-trifluoromethylhexyloxycarbonyl)benzene. This product was analyzed by thin film chromatography to show that benzylacetamide was co-present in addition to the end product.

Workup

  1. customAfter the reaction
  2. extractionsubjected to extraction with dichloromethane
  3. washAn organic layer was consecutively washed with a hydrochloric acid aqueous solution and with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-743ae2efa11a478ca5343f9e3709749b
Source dataset
uspto-grants-1998_05
Patent number
US05756816

Reaction notes

Loading…