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

HRID 36419Notes

Reaction equation

HRID 36419 reaction equation
C(O)=O.C(N(CC)CC)C.CC1(C)[O:19][C:17](=[O:18])[CH2:16][C:14](=O)O1.C(=O)[C:22]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[C:24]([O:25][CH3:26])[CH:23]=1>C(#N)C>[CH3:26][O:25][C:24]1[CH:23]=[C:22]([CH2:14][CH2:16][C:17]([OH:19])=[O:18])[CH:31]=[CH:30][C:27]=1[O:28][CH3:29]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8419VeratraldehydeHCID 8471TriethylamineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 750193-(3,4-Dimethoxyphenyl)propionic acidYield 68.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

After adding 2.1 ml of the mixture of formic acid and triethylamine prepared as described in Example 1 to 20 ml of acetonitrile, 3.60 g (0.025 mol) of Meldrum's acid and 4.15 g (0.025 mol) of veratraldehyde were added to the reaction mixture. After heating same to its boiling point (82° C.) within 30 minutes and refluxing it for 4 hours, the acetonitrile was evaporated under reduced pressure, then the method of Example 1 was followed to give 3.6 g of a product, m.p.: 91°-93.5° C., which was recrystallized from aqueous methanol of 50% by volume.

Workup

  1. customprepared
  2. additionwere added to the reaction mixture
  3. temperaturerefluxing it for 4 hours
  4. customthe acetonitrile was evaporated under reduced pressure

Sources & evidence

ORD record
ord-80f6fc405bd84b009b1ee677aa213c3d
Source dataset
uspto-grants-1995_05
Patent number
US05414108

Reaction notes

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