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

HRID 2294965ノート

反応式

HRID 2294965 の反応式
[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]

参加物

5

反応物 2

HCID 12252872Ethyl 3-allyl-4-hydroxybenzoateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 14986319Ethyl 4-hydroxy-3-propylbenzoate収率 115.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-95dee93b60f44bc8b17c1c6c1e8f78a8
出典データセット
uspto-grants-1997_11
特許番号
US05691349

反応ノート

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