Malonic Acid → HCID 70374992, compound

HRID 370409Notes

Reaction equation

HRID 370409 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[C:8]([O:15][CH3:16])=[C:7](C)[C:4]=1[CH:5]=O.[C:18](O)(=O)[CH2:19][C:20]([OH:22])=[O:21].N1CCCCC1>N1C=CC=CC=1>[CH3:16][O:15][C:8]1([CH:7]=[C:4]([CH3:5])[C:3]([O:2][CH3:1])=[C:10]([O:11][CH3:12])[CH:9]1[O:13][CH3:14])[CH:18]=[CH:19][C:20]([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehyde

Product 1

HCID 70374992HCID 70374992, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,3,4,5-Tetramethoxy-6-methylbenzaldehyde (17.3 g, 72.1 mmol), malonic acid (22.5 g, 216 mmol) and piperidine (1.7 ml) were dissolved in pyridine (50 ml). The reaction was conducted for 5 hours, while the temperature was gradually raised from 50° C. to 100° C. The solvent was removed under reduced pressure. The residue was acidfified with 2 N hydrochloric acid, extracted and concentrated. Recrystallization of the product from ethyl acetate-isopropyl ether gave 1,2,3,4-tetramethoxy-5-methylcinnamic acid (Compound 20, 14.3 g, 70%). m.p. 117°-118° C. δ 2.31 (3H), 3.78 (3H), 3.83 (3H), 3.90 (3H), 3.96 (3H), 6.59 (1H), 7.94 (1H), 11.2 (1H).

Workup

  1. temperaturewas gradually raised from 50° C. to 100° C
  2. customThe solvent was removed under reduced pressure
  3. extractionextracted
  4. concentrationconcentrated
  5. customRecrystallization of the product from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-0d1933d40f5b4b54ac6d2d1ac197324d
Source dataset
uspto-grants-1985_07
Patent number
US04526719

Reaction notes

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