Acetic Acid → 2-Methylfluorene

HRID 1089826

반응식

HRID 1089826 반응식
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=O.C(O)(=O)C.[H][H]>C(OCC)(=O)C.CCCCCC.[OH-].[OH-].[Pd+2]>[CH3:14][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:12][C:13]=2[CH:1]=1

참가 물질

7

반응물 3

HCID 176Acetic AcidHCID 34804Fluorene-2-carboxaldehydeHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 150262-Methylfluorene수율 69.1%

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of 2-fluorenecarboxaldehyde (15 g, 77.1 mmol) in 250 mL of 10% solution of acetic acid in ethyl acetate was hydrogenated at 80 psi of hydrogen during 24 hours at room temperature over 20% palladium hydroxide on carbon (catalytic amount). The reaction was monitored by TLC (silica, 25% ethyl acetate in hexane). The catalyst was filtered off, evaporation of the solvents followed by recrystallization of the residual solid from ethanol:water 5:1 afforded 9.6 g (69.0%) of the product as colorless solid.

후처리

  1. filtrationThe catalyst was filtered off
  2. customevaporation of the solvents
  3. customfollowed by recrystallization of the residual solid from ethanol:water 5:1

출처 및 근거

ORD 기록
ord-8f6e1c3af9924fbfa04f62eb84f9198e
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05079260

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