Thionyl Chloride → HCID 20320785, compound

HRID 866397Notes

Reaction equation

HRID 866397 reaction equation
O[CH:2]=[CH:3][C:4]([C:6]1([CH3:13])[CH2:9][C:8]2([CH2:12][CH2:11][CH2:10]2)[CH2:7]1)=[O:5].S(Cl)([Cl:16])=O>C1C=CC=CC=1>[Cl:16]/[CH:2]=[CH:3]/[C:4]([C:6]1([CH3:13])[CH2:9][C:8]2([CH2:12][CH2:11][CH2:10]2)[CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 85919270HCID 85919270, compound

Product 1

HCID 20320785HCID 20320785, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4.0 g of (2-methylspiro[3.3]hept-2-yl) (2-hydroxyvinyl) ketone in 25.0 ml of benzene was added dropwise with stirring to 3.95 g of thionyl chloride. The reaction mixture was allowed to stand for 18 hr at 25° C. The product was isolated by distillation (high vacuum) to afford 2.66 g 1-chloro-3-(2-methylspiro[3.3]hept-2-yl)-1E-propen-3-one as a yellow oil (40%).

Workup

  1. customThe product was isolated by distillation (high vacuum)

Sources & evidence

ORD record
ord-392c35bd1a874234ab197a94597d834d
Source dataset
uspto-grants-1978_07
Patent number
US04098823

Reaction notes

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