Thionyl Chloride → 5-Chloro-5H-dibenzo[a,d][7]annulene

HRID 2290281Notes

Reaction equation

HRID 2290281 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6](O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:19])=O>C1C=CC=CC=1>[Cl:19][CH:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[CH:10]=[CH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]1=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 82577Dibenzosuberenol

Product 1

HCID 110751355-Chloro-5H-dibenzo[a,d][7]annulene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5.00 grams (24 millimoles) of 5H-dibenzo[a,d]cyclohepten-5-ol and 8.57 grams (72 millimoles) of thionyl chloride were heated together in refluxing benzene for 0.5 hour, then the solvent was vaporized to obtain a 5-chloro-5H-dibenzo[a,d]cycloheptene intermediate as residue.

Sources & evidence

ORD record
ord-8199a881410643b6bc03031f323d257e
Source dataset
uspto-grants-1986_10
Patent number
US04616023

Reaction notes

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