Ethyl 3-allyl-4-hydroxybenzoate → Ethyl 4-hydroxy-3-propylbenzoate

HRID 2294965노트

반응식

HRID 2294965 반응식
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][CH:13]=[CH2:14])[CH:6]=1)[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][CH2:13][CH3:14])[CH:6]=1)[CH3:2]

참가 물질

5

반응물 2

HCID 12252872Ethyl 3-allyl-4-hydroxybenzoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 14986319Ethyl 4-hydroxy-3-propylbenzoate수율 115.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A mixture of ethyl-3-allyl-4-hydroxybenzoate (4.12 g), palladium on carbon (10% w/w) and ethanol (100 ml) was stirred under an atmosphere of hydrogen until 500 ml of hydrogen had been consumed. The mixture was filtered and the filtrate was evaporated. The residue was purified by flash chromatography on silica gel using 4:1 (v/v) n-pentane/ethyl acetate as eluent to give ethyl-3-propyl-4-hydroxybenzoate (4.8 g) as a solid, m.p. 78°-79° C.; microanalysis, found: C, 69.2; H, 8.1%; C12H16O3 requires: C, 69.2; H, 7.74%; NMR (CDCl3): 0.97(3H,t), 1.38(3H,t), 1.67(2H,m), 2.60(2H,t), 4.35(2H,q), 5.71(1H,s), 6.79(1H,d) and 7.75-7.87(2H,m); m/z 209(M+H).

후처리

  1. customhad been consumed
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by flash chromatography on silica gel using 4:1 (v/v) n-pentane/ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-95dee93b60f44bc8b17c1c6c1e8f78a8
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05691349

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