Acetic Acid → Ferulic Acid

HRID 1611752Notes

Reaction equation

HRID 1611752 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1.C(O)(=O)C>CCCCCC.CO>[C:14]([OH:16])(=[O:15])/[CH:13]=[CH:2]/[C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 867Malonic AcidHCID 1183VanillinHCID 8082Piperidine

Product 1

HCID 445858Ferulic AcidYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

A mixture of vanillin (2.50 g, 0.0164 mol), malonic acid (3.41 g; 0.0328 mol), piperidine (3–5 mL) and acetic acid (10–20 mL) were taken in a round bottom flask and the reaction mixture was refluxed for 5–6 hours instead of microwave irradiation as mentioned in Example I. The cooled mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with dil HCl., saturated sodium chloride and then organic layer dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain solid which was recrytallised with mixture of methanol and hexane, provided ferulic acid as a solid compound mp 169° C. (lit mp 168–171° C.) in 65% yield; 1H NMR (DMSO-d6) δ 12.13 (1H, s, COOH), 7.48 (1H, d, Ar—CH═CH—COOH), 7.27 (1H, s, H-3), 7.07 (1H, d, H-6), 6.78 (1H, d, H-5), 6.36 (1H, d, —CH═CH—COOH), 3.81 (3H, s, 2-OCH3); δ168.9 (COOH), 149.8 (C-1), 148.7 (C-2), 145.4 (CH═CH—COOH), 126.6 (C-4), 123.7 (C-5), 116.4 (C-3 & C-6), 111.8 (CH═CH—COOH), 56.4 (2-OCH3).

Workup

  1. customwere taken in a round bottom flask
  2. temperaturethe reaction mixture was refluxed for 5–6 hours instead of microwave irradiation
  3. additionThe cooled mixture was poured into ice-cold water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with dil HCl
  6. dry with material, saturated sodium chloride and then organic layer dried over sodium sulphate
  7. customThe solvent was evaporated under reduced pressure
  8. customto obtain solid which

Sources & evidence

ORD record
ord-c40a9b64cc3e45919e8c76047d1408b5
Source dataset
uspto-grants-2006_01
Patent number
US06989467B2

Reaction notes

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