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

HRID 866931Notes

Reaction equation

HRID 866931 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 1g of potassium hydroxide dissolved in 1ml of water and 4ml of ethanol was added 106mg 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-8311df88ee12448f9915213e96a8cecb
Source dataset
uspto-grants-1978_07
Patent number
US04101667

Reaction notes

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