Water → Dibenzo(b,f)thiepin-1-carboxylic acid, 10,11-dihydro-8-methoxy-

HRID 866937Notes

Reaction equation

HRID 866937 reaction equation
[OH-:1].[K+].[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]2[S:9][C:10]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#N)[C:11]=3[CH2:12][CH2:13][C:7]=2[CH:6]=1.[OH2:22]>C(O)C>[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]2[S:9][C:10]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([OH:22])=[O:1])[C:11]=3[CH2:12][CH2:13][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 233370482-Methoxy-9-cyano-10,11-dihydrodibenzo[b,f]thiepin

Product 1

HCID 3045903Dibenzo(b,f)thiepin-1-carboxylic acid, 10,11-dihydro-8-methoxy-Yield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An amount of 6.0g potassium hydroxide was dissolved in 20ml of 80% ethanol and to the solution was added 1g of 2-methoxy-9-cyano-10,11-dihydrodibenzo[b,f]thiepin and the resulting mixture was refluxed for 26 hours. The mixture was freed of the solvent under reduced pressure to obtain the residue, which was dissolved in water and extracted with ethyl acetate. The aqueous layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and freed of the solvent to give 743 mg (69%) of 2-methoxy-9-carboxy-10,11-dihydrodibenzo[b,f]thiepin as pale reddish needles having a melting point of 185°-186° C.

Workup

  1. temperaturethe resulting mixture was refluxed for 26 hours
  2. customto obtain the residue, which
  3. extractionextracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-78294fe96ff244f2a6ef9ec7869ed128
Source dataset
uspto-grants-1978_07
Patent number
US04101667

Reaction notes

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