Reaction #56242

Reaction equation

hydrochloric acid

sodium hydride

9-formyl-9,10-dihydro-9,10-methanoanthracene

β-carboxyethyltriphenylphosphonium chloride

dimethylsulfoxide

→

γ-(9,10-dihydro-9,10-methano-9-anthryl)-β-butenoic acid

Solvents

water

tetrahydrofuran

Conditions

Workup

1. 1
   Extractionextracted with benzene
2. 2
   ExtractionThe benzene extract
3. 3
   workup.STIRRINGwas shaken with 2 N aqueous sodium hydroxide
4. 4
   Extractionextracted with ethyl acetate
5. 5
   ExtractionThe ethyl acetate extract
6. 6
   Washwas washed with water
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   Otherevaporated to dryness

Procedure

To a mixture of 9-formyl-9,10-dihydro-9,10-methanoanthracene (110 mg) and β-carboxyethyltriphenylphosphonium chloride (186 mg) in dimethylsulfoxide (2 ml) and tetrahydrofuran (2 ml) was added 65.4% sodium hydride dispersion in mineral oil (37 mg) at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 6 hours, diluted with water, acidified with hydrochloric acid and extracted with benzene. The benzene extract was shaken with 2 N aqueous sodium hydroxide. The basic layer was acidified with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give γ-(9,10-dihydro-9,10-methano-9-anthryl)-β-butenoic acid. M.P. 166°-167° C.

Source