Veratrole → HCID 15680654, compound

HRID 2254326Notes

Reaction equation

HRID 2254326 reaction equation
[C:1](O)(=[O:7])[CH2:2][CH2:3][C:4]([CH3:6])=[O:5].ClCC(OC(=O)CCl)=O.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27]>ClC(Cl)C>[C:4]([CH2:3][CH2:2][C:1]([C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[C:21]([O:26][CH3:27])[CH:22]=1)=[O:7])(=[O:5])[CH3:6]

Participants

5

Reactant 3

HCID 7043VeratroleHCID 10946Chloroacetic anhydrideHCID 11579Levulinic Acid

Product 1

HCID 15680654HCID 15680654, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

In 50 ml of dichloroethane were dissolved 5.8 g (0.05 mole) of levulinic acid and 10.26 g (0.06 mole) of monochloroacetic anhydride. To the resulting solution were added 8.98 g (0.065 mole) of 1,2-dimethoxybenzene and 0.71 g of boron trifluoride-diethyl ether complex and the resulting mixture was then stirred at 50° C. for 5.5 hours. After completion of the reaction, the reaction solution was cooled and washed successively with water, 5% aqueous sodium carbonate solution and water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 9.66 g of 4-(β-acetylpropionyl)-1,2-dimethoxybenzene.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled
  3. washwashed successively with water, 5% aqueous sodium carbonate solution and water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a319651bcfc4d3bacc9baa443fbf498
Source dataset
uspto-grants-1993_08
Patent number
US05235068

Reaction notes

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