Hydrochloric Acid → gamma-(9,10-Dihydro-9,10-methano-9-anthryl)-beta-butenoic acid

HRID 27964

Reaction equation

C([C:3]12[CH2:17][CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=31)[C:9]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:8]=1)=O.[Cl-].[C:19]([CH2:22][CH2:23][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:21])=[O:20].[H-].[Na+].Cl.[CH3:46]S(C)=O>O1CCCC1.O>[CH:15]1[C:16]2[C:3]3([CH:46]=[CH:23][CH2:22][C:19]([OH:21])=[O:20])[CH2:17][CH:10]([C:9]4[C:8]3=[CH:7][CH:6]=[CH:5][CH:4]=4)[C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

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.

Workup

extractionextracted with benzene
extractionThe benzene extract
stirringwas shaken with 2 N aqueous sodium hydroxide
extractionextracted with ethyl acetate
extractionThe ethyl acetate extract
washwas washed with water
dry with materialdried over anhydrous sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-6a1bcab99e7646dca3cfbb7012c89a4b
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04224344

Linked notes

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