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

HRID 27964

反応式

HRID 27964 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6a1bcab99e7646dca3cfbb7012c89a4b
出典データセット
uspto-grants-1980_09
特許番号
US04224344

関連ノート

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