Ethanol → 3-(4-Tert-butylphenyl)propanoic acid

HRID 1017145노트

반응식

HRID 1017145 반응식
C([C:5](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])(C)(C)C.O1[CH2:20][CH2:19][CH2:18]C1.[H][H].[CH2:23](O)C>[Pd]>[C:19]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH2:5][C:6]([OH:8])=[O:7])=[CH:15][CH:14]=1)([CH3:18])([CH3:20])[CH3:23]

참가 물질

6

반응물 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 54357124t-Butylcinnamic acidHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 49621733-(4-Tert-butylphenyl)propanoic acid

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

A 3 L autoclave was charged with wet t-butylcinnamic acid (248 g, 1.21 mol), tetrahydrofuran (1 L), and ethanol (1 L) and palladium on carbon (35 g). The reactor was shut and 90 psi of hydrogen pressure applied and the reactor held at room temperature overnight. The reaction was then transferred to a round bottom flask and concentrated to 200 mL. The formed crystals were decanted and washed with hexane to give 3-(4-t-butylphenyl)propionic acid (52.9 g after vacuum drying). A second crop from the filtrate yielded additional 3-(4-t-butylphenyl)propionic acid (65.8 g). 1HNMR (CD2Cl2, 500 MHz) δ9.85 (br s, 1H); 7.32 (d, J=8 Hz, 2H); 7.15 (d, JAB=8.5 Hz); 2.91 (t, J=8 Hz, 2H); 2.67 (t, J=8 Hz, 2H); 1.27 (s, 9H).

후처리

  1. customThe reaction was then transferred to a round bottom flask
  2. concentrationconcentrated to 200 mL
  3. customThe formed crystals were decanted
  4. washwashed with hexane

출처 및 근거

ORD 기록
ord-da68f309293546e392a33db547bf6e40
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479424B1

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