Dibenzosuberol → 5H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro-

HRID 1981183Notes

Reaction equation

HRID 1981183 reaction equation
S(Cl)([Cl:3])=O.[CH:5]1[C:15]2[CH2:14][CH2:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[CH:10](O)[C:9]=2[CH:8]=[CH:7][CH:6]=1>C1C=CC=CC=1>[Cl:3][CH:10]1[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:15]=2[CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]1=2

Participants

4

Reactant 2

HCID 14588DibenzosuberolHCID 24386Thionyl Chloride

Product 1

HCID 145875H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

350 ml of thionyl chloride are added dropwise at a temperature of 30 to 40° to a solution of 201.5 g of crude 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol in 700 ml of dry benzene over a period of 40 minutes. Subsequently, the mixture is heated to boiling under reflux for an additional 1.5 hours and concentrated in vacuo. The residue is diluted 2 to 3 times with 300 ml of benzene each time and in each case again evaporated. There is obtained 5-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as a beige crystalline mass of melting point 99-101° which is used in the next step without further purification. By recrystallization from carbon tetrachloride there is obtained material of melting point 104°-105° C.

Workup

  1. temperatureSubsequently, the mixture is heated
  2. temperatureunder reflux for an additional 1.5 hours
  3. concentrationconcentrated in vacuo
  4. additionThe residue is diluted 2 to 3 times with 300 ml of benzene each time
  5. customin each case again evaporated

Sources & evidence

ORD record
ord-87f5ca0bdb56446c92665a4bd57c673b
Source dataset
uspto-grants-1985_04
Patent number
US04513002

Reaction notes

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