Chloroform → HCID 20310684, compound

HRID 259027Notes

Reaction equation

HRID 259027 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]2[C:8](=[O:17])[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[CH:11]=[CH:12][C:6]=2[CH:5]=1)(O)=[O:2].C(Cl)(Cl)[Cl:21].S(Cl)(Cl)=O>CN(C)C=O>[Cl:21][C:1]([C:4]1[CH:19]=[CH:18][C:7]2[C:8](=[O:17])[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[CH:11]=[CH:12][C:6]=2[CH:5]=1)=[O:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 125630012-carboxy-5-oxo-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 20310684HCID 20310684, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.0 g. of 2-carboxy-5-oxo-5H-dibenzo[a,d]cycloheptene is dissolved in 100 ml. of chloroform, and 50 ml. of thionyl chloride and 1.0 ml. of dimethylformamide are added thereto. The mixture is left for 3 days, then evaporated to dryness to afford 2-chlorocarbonyl-5-oxo-5H-dibenzo[a,d]cycloheptene. 1.0 G. of this compound is dissolved in 10 ml. of tetrahydrofuran containing 1.0 ml. of isopentyl alcohol and 2 ml. of pyridine. The mixture is left for 24 hours, then evaporated to dryness, dissolved in 1:4 ether/hexane and filtered through silica gel, then evaporated to give isopentyl (5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)carboxylate (m.p. 26°-30° C).

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-273a027f10534dc890f72a20de97e39b
Source dataset
uspto-grants-1977_07
Patent number
US04035509

Reaction notes

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