Water → 2-Hydroxy-9-carboxy-10,11-dihydrodibenzo[b,f]thiepin

HRID 866936Notes

Reaction equation

[OH-:1].[Na+].C[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)COCCO>[OH: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

Conditions

Temperature: 200 °C

Procedure

An amount of 2.2g of sodium hydroxide was dissolved in 30ml of diethylene glycol by application of heat and to the mixture was added 2.2g of 2-methoxy-9-cyano-10,11-dihydrodibenzo[b,f]thiepin and the resulting mixture was stirred at 200° C for 16 hours. After cooling, to the mixture was added water and the mixture was extracted with ethyl acetate. The equeous layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate. This extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and freed of the solvent to obtain the residue. This residue was recrystallized from benzene to afford 1.1g (46%) of 2-hydroxy-9-carboxy-10,11-dihydrodibenzo[b,f]thiepin as brown crystals having a melting point of 210°-211° C.

Workup

temperatureof heat and to the mixture
temperatureAfter cooling, to the mixture
extractionthe mixture was extracted with ethyl acetate
extractionextracted with ethyl acetate
washThis extract was washed with saturated sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
customto obtain the residue
customThis residue was recrystallized from benzene

Sources & evidence

ORD record: ord-9ddbed6ebfaa4e00a04faccfdbc7a43c
Source dataset: uspto-grants-1978_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04101667

Reaction notes

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