Ethanol → 2-Trifluoromethyl-10,11-dihydrodibenzo[b,f]thiepin-9-carboxylic acid

HRID 261564Notes

Reaction equation

HRID 261564 reaction equation
[OH-:1].[K+].[CH2:3]([OH:5])[CH3:4].[F:6][C:7]([F:26])([F:25])[C:8]1[CH:24]=[CH:23][C:11]2[S:12][C:13]3[CH:20]=[CH:19][CH:18]=C(C#N)[C:14]=3[CH2:15][CH2:16][C:10]=2[CH:9]=1.[OH-].[Na+]>O.CCOCC>[F:6][C:7]([F:26])([F:25])[C:8]1[CH:24]=[CH:23][C:11]2[S:12][C:13]3[CH:20]=[CH:19][CH:18]=[C:4]([C:3]([OH:1])=[O:5])[C:14]=3[CH2:15][CH2:16][C:10]=2[CH:9]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 126871222-Trifluoromethyl-9-cyano-10,11-dihydrodibenzo[b,f]thiepin

Product 1

HCID 126871242-Trifluoromethyl-10,11-dihydrodibenzo[b,f]thiepin-9-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 1 g of potassium hydroxide dissolved in 1 ml of water and 4 ml of ethanol was added 106 mg of 2-trifluoromethyl-9-cyano-10,11-dihydrodibenzo[b,f] thiepin and the resulting mixture was refluxed for 24 hrs. After cooling, to this was added 4% sodium hydroxide solution and ether. After shaking, the aqueous layer was separated, acidified by adding conc. hydrochloric acid and extracted with chloroform. Extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 87 mg (77.3% of yield) of the desired product as colorless powder. This was recrystallized from the mixed solvent of benzene and n-hexane to afford 2-trifluoromethyl-10,11-dihydrodibenzo[b,f]thiepin-9-carboxylic acid having a melting point of 178.5° to 179.5° C. as colorless crystals.

Workup

  1. temperaturethe resulting mixture was refluxed for 24 hrs
  2. temperatureAfter cooling
  3. customthe aqueous layer was separated
  4. additionby adding conc. hydrochloric acid
  5. extractionextracted with chloroform
  6. extractionExtract
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated
  10. customto obtain

Sources & evidence

ORD record
ord-15f2c54e29f3451186675c8ac7dc2236
Source dataset
uspto-grants-1979_08
Patent number
US04166127

Reaction notes

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