Formic Acid → 3-(3,4-Dimethoxyphenyl)propionic acid

HRID 36423Notes

Reaction equation

HRID 36423 reaction equation
CC1(C)[O:9][C:7](=[O:8])[CH2:6][C:4](=O)O1.C(=O)[C:12]1[CH:21]=[CH:20][C:17]([O:18][CH3:19])=[C:14]([O:15][CH3:16])[CH:13]=1.C(OCC)(=O)C.C(O)=O>C(N(CC)CC)C>[CH3:16][O:15][C:14]1[CH:13]=[C:12]([CH2:4][CH2:6][C:7]([OH:9])=[O:8])[CH:21]=[CH:20][C:17]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8419VeratraldehydeHCID 8857Ethyl AcetateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 750193-(3,4-Dimethoxyphenyl)propionic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A reaction mixture containing 14.4 g (0.1 mol) of Meldrum's acid, 16.6 g (0.1 mol) of veratraldehyde, 100 ml of ethyl acetate and 25 ml of the mixture of formic acid and triethylamine prepared as described in Example 1 was heated to its boiling point during 1 hour and then refluxed for 6 hours. After distilling off the ethyl acetate under reduced pressure, the distillation residue was cooled to room temperature, 100 ml of water were added and the pH value of the mixture was adjusted to 1 with concentrated hydrochloric acid, then the method described in Example 1 was followed.

Workup

  1. customprepared
  2. temperaturewas heated to its boiling point during 1 hour
  3. temperaturerefluxed for 6 hours
  4. distillationAfter distilling off the ethyl acetate under reduced pressure
  5. addition100 ml of water were added

Sources & evidence

ORD record
ord-337409d624254d0e9806a31675f5acea
Source dataset
uspto-grants-1995_05
Patent number
US05414108

Reaction notes

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