Acetic Acid → HCID 178472486, 화합물

HRID 271344노트

반응식

HRID 271344 반응식
[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]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 8434EthylparabenHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 178472486HCID 178472486, 화합물수율 106.1%

시약·촉매·용매 2

HCID 23948Rhodium촉매HCID 702Ethanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3ca0c3b196a44368890c7a7d69b34294
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452893B2

반응 노트

불러오는 중…