Hydrochloric Acid → HCID 10333006, compound

HRID 1373449Notes

Reaction equation

HRID 1373449 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.S(OCC)(O[CH2:12][CH3:13])(=O)=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30].Cl>ClC1C=CC=CC=1>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([C:4](=[O:5])/[CH:3]=[CH:2]/[C:1]([O:6][CH2:12][CH3:13])=[O:7])[CH:26]=[CH:25][C:24]=1[O:29][CH3:30]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6163Diethyl SulfateHCID 7043VeratroleHCID 7923Maleic AnhydrideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 10333006HCID 10333006, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
10 °C

Procedure

Into a 500 ml four-neck flask were charged 66.9 g (0.682 mol) of maleic anhydride, 150 ml of chlorobenzene, 71.6 ml (0.546 mol) of diethyl sulfate under a nitrogen atmosphere. Then, the whole was cooled to 10° C. or lower and 67.6 g (0.507 mol) of aluminum chloride was added thereto. While temperature was maintained at 10 to 15° C., 25 ml (0.195 mol) of 1,2-dimethoxybenzene was added dropwise, followed by 4 hours of reaction. After termination of the reaction was confirmed by HPLC analysis, the reaction solution was added dropwise to 200 ml of a 1N hydrochloric acid aqueous solution cooled to 0° C. to decompose excess aluminum chloride. After liquid separation, the organic layer was washed with 200 ml of a 10% sodium bicarbonate aqueous solution to remove excess maleic anhydride. After the solvent was removed by evaporation under reduced pressure, the residue was crystallized from 5 ml of ethanol to obtain 36.2 g (yield 70.3%) of the aimed compound as light yellow crystals. As a result of HPLC analysis, the purity was found to be 99.8%.

Workup

  1. temperatureWhile temperature was maintained at 10 to 15° C.
  2. customfollowed by 4 hours of reaction
  3. temperaturecooled to 0° C.
  4. customAfter liquid separation
  5. washthe organic layer was washed with 200 ml of a 10% sodium bicarbonate aqueous solution
  6. customto remove excess maleic anhydride
  7. customAfter the solvent was removed by evaporation under reduced pressure
  8. customthe residue was crystallized from 5 ml of ethanol

Sources & evidence

ORD record
ord-5fcac8fe644e46a4becc40160c4123c6
Source dataset
uspto-grants-2007_01
Patent number
US07161022B2

Reaction notes

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