Veratrole → 4-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

HRID 1375698Notes

Reaction equation

HRID 1375698 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[C:11]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12]1.[Al+3].[Cl-].[Cl-].[Cl-]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:5][C:4]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7043VeratroleHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2193904-(3,4-Dimethoxyphenyl)-4-oxobutanoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

11.4 g (0.09 mol) of 1,2-dimethoxybenzene are mixed with 3 g (0.03 mol) of succinic anhydride, and then, under stirring, the semisolid mass is added with 7.8 g (0.06 mol) of AlCl3 under a light nitrogen flow. After 24 hours at room temperature under a nitrogen atmosphere, 300 ml of ethyl ether are added. A precipitate is formed which is filtered and treated by cooling with 100 ml of HCl 6N, extracting several times with CH2Cl2 and washing with water. The organic solution, anhydrified with anhydrous sodium sulphate, is concentrated to dryness, obtaining a yellow solid which is crystallised by n-hexane/EtOAc giving 3 g of product. Yield 50%.

Workup

  1. customA precipitate is formed which
  2. filtrationis filtered
  3. additiontreated
  4. temperatureby cooling with 100 ml of HCl 6N
  5. extractionextracting several times with CH2Cl2
  6. washwashing with water
  7. concentrationis concentrated to dryness
  8. customobtaining a yellow solid which
  9. customis crystallised by n-hexane/EtOAc giving 3 g of product

Sources & evidence

ORD record
ord-2d4f1f82330d4122a03810729a5dfde7
Source dataset
uspto-grants-2007_01
Patent number
US07169808B2

Reaction notes

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