Acetic Acid → HCID 178472486、化合物

HRID 271344ノート

反応式

HRID 271344 の反応式
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(O)(=O)C.[H][H]>[Rh].C(O)C>[CH2:9]([O:8][C:6]([C@H:5]1[CH2:11][CH2:12][C@@H:2]([OH:1])[CH2:3][CH2:4]1)=[O:7])[CH3:10]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 8434EthylparabenHCID 178418361HCID 178418361、化合物

生成物 1

HCID 178472486HCID 178472486、化合物収率 106.1%

試薬・触媒・溶媒 2

HCID 23948Rhodium触媒HCID 702Ethanol溶媒

実験手順

A mixture of 10 g of ethyl 4-hydroxybenzoate, 5 mL of acetic acid, 0.8 g of 5% rhodium on alumina, and 200 mL of ethanol was shaken under 55 psi of hydrogen for 48 h, filtered and concentrated under reduced pressure. The residue was taken up in 200 mL of toluene and again concentrated under reduced pressure to remove acetic acid. Drying under vacuum overnight gave 11 g of product, which was predominantly cis (83:17 cis: trans by HPLC), as a colorless oil: MS (m+1)=173.2; 1H NMR (400 MHz, CDCl3) 4.1 (dd, 2H), 3.9 (m, cis isomer, 0.85H), 3.6 (m, trans isomer, 0.15H), 2.4 and 2.2 (m, 1H), 2.0 (m, 2H), 1.62 (m, 6H), 1.2 (t, 3H).

後処理

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. concentrationagain concentrated under reduced pressure
  4. customto remove acetic acid
  5. customDrying under vacuum overnight

出典と根拠

ORDレコード
ord-3ca0c3b196a44368890c7a7d69b34294
出典データセット
uspto-grants-2008_11
特許番号
US07452893B2

反応ノート

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