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

HRID 27964

반응식

HRID 27964 반응식
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

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 10270534(2-Carboxyethyl)triphenylphosphonium chlorideHCID 124041419,10-Methanoanthracene-9(10H)-carbaldehyde

생성물 1

HCID 54474651gamma-(9,10-Dihydro-9,10-methano-9-anthryl)-beta-butenoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  1. extractionextracted with benzene
  2. extractionThe benzene extract
  3. stirringwas shaken with 2 N aqueous sodium hydroxide
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-6a1bcab99e7646dca3cfbb7012c89a4b
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04224344

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