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

HRID 36411

Reaction equation

HRID 36411 reaction equation
C(O)=O.C(N(CC)CC)C.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:21][CH:22]2C(=O)OC(C)(C)[O:24][C:23]2=[O:31])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].Cl>C(Cl)(Cl)Cl.O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:21][CH2:22][C:23]([OH:31])=[O:24])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 103346195-(3,4-Dimethoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

After adding 2.5 ml of the mixture of formic acid and triethylamine prepared according to Example 1 to 2.94 g (0.01 mol) of 5-(3,4-dimethoxyphenylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (m.p.: 142°-144° C.), the reaction mixture was heated to 100° C. for 2 hours, then cooled down. After the addition of 25 ml of water the pH value was adjusted to 1 by adding concentrated hydrochloric acid, then the mixture was thoroughly shaken with 100 ml of chloroform. After separation the chloroform phase was evaporated under reduced pressure to give a white crystalline product.

Workup

  1. customprepared
  2. temperaturecooled down
  3. customAfter separation the chloroform phase
  4. customwas evaporated under reduced pressure
  5. customto give a white crystalline product

Sources & evidence

ORD record
ord-b94fb2c2aa4547d582d45a9b25ab0e89
Source dataset
uspto-grants-1995_05
Patent number
US05414108

Linked notes

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