Veratrole → HCID 12238904, compound

HRID 2254337Notes

Reaction equation

HRID 2254337 reaction equation
[C:1]1([C:7](O)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.ClCC(OC(=O)CCl)=O.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH3:28]>ClC(Cl)C>[C:1]1([C:7]([C:24]2[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[C:22]([O:27][CH3:28])[CH:23]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 7043VeratroleHCID 10946Chloroacetic anhydrideHCID 694701-Cyclohexene-1-carboxylic acid

Product 1

HCID 12238904HCID 12238904, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
75 °C

Procedure

In 50 ml of dichloroethane were dissolved 6.31 g (0.05 mole) of 1-cyclohexene-1-carboxylic 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 trifluoridediethyl ether complex and the resulting mixture was then stirred at 75° C. for 6 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 7.27 g of 4-(1-cyclohexenoyl)-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-e4a777fb3fc545cfb787a2ffc68ecb86
Source dataset
uspto-grants-1993_08
Patent number
US05235068

Reaction notes

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