Acetic Acid → HCID 178472486, compound

HRID 271344Notes

Reaction equation

HRID 271344 reaction equation
[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]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8434EthylparabenHCID 178418361HCID 178418361, compound

Product 1

HCID 178472486HCID 178472486, compoundYield 106.1%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-3ca0c3b196a44368890c7a7d69b34294
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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