Protocatechuic Acid → Methyl 3,4-Dihydroxybenzoate

HRID 1089528Notes

Reaction equation

HRID 1089528 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].Cl[CH:13](Cl)C.CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:13][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([OH:1])[CH:3]=1

Participants

6

Reactant 4

HCID 72Protocatechuic AcidHCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 63651,1-Dichloroethane

Product 1

HCID 287064Methyl 3,4-Dihydroxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 180 g of 3,4-dihydroxybenzoic acid, 360 ml of dichloroethane, 142 ml of methanol and 18 g of p-toluenesulfonic acid was boiled on a water separator, until distillate is clear. The solvent was evaporated, and the residue was admixed with 1.5 liters of diethyl ether, washed with 1 liter of a saturated aqueous sodium bicarbonate solution and twice with each 0.4 liter of aqueous sodium chloride solution. After evaporation again, the residue was recrystallized from 3 liters of toluene to obtain the product. m.p. 136°-137° C.

Workup

  1. customThe solvent was evaporated
  2. washwashed with 1 liter of a saturated aqueous sodium bicarbonate solution and twice with each 0.4 liter of aqueous sodium chloride solution
  3. customAfter evaporation again
  4. customthe residue was recrystallized from 3 liters of toluene
  5. customto obtain the product

Sources & evidence

ORD record
ord-73a0387ddf2940d6a00ba0cc482175ba
Source dataset
uspto-grants-1990_10
Patent number
US04966900

Reaction notes

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