Potassium Carbonate → HCID 68924095, compound

HRID 2375553Notes

Reaction equation

HRID 2375553 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12](=[O:27])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([O:21]C(=O)C)=[C:17]([O:25][CH3:26])[CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O1CCCC1.O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12](=[O:27])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:25][CH3:26])[CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 68927469HCID 68927469, compound

Product 1

HCID 68924095HCID 68924095, compoundYield 56.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-3-[4-acetyloxy-3-methoxyphenyl]-2-propenoic acid 4-(acetylamino)phenyl ester (4.2 g, 11.37 mmoles) in methanol (650 ml) and tetrahydrofuran (850 ml), potassium carbonate (9.11 g, 65.95 mmoles) dissolved in water (50 ml) is added and it is left under stirring at room temperature for 2 hours. The precipitate is filtered and the solution is brought to pH 6 with HCl 5% (15 ml). One extracts with ethyl acetate and the organic phase is anhydrified and removed from the solvent at reduced pressure. The raw product is purified by chromatography on silica gel eluting with chloroform/methanol (9/0.5 v/v). Trans-3-[4-hydroxy-3-methoxyphenyl]-2-propenoic acid 4-(acetylamino)phenyl ester (2.1 g) is obtained as a white solid. M.p. 185-195° C. Yield 56%.

Workup

  1. additionis added
  2. waitit is left
  3. filtrationThe precipitate is filtered
  4. customremoved from the solvent at reduced pressure
  5. customThe raw product is purified by chromatography on silica gel eluting with chloroform/methanol (9/0.5 v/v)

Sources & evidence

ORD record
ord-b968ea7051b04bde98432af5890b0677
Source dataset
uspto-grants-2008_12
Patent number
US07465803B2

Reaction notes

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