Protocatechuic Acid → HCID 22419537, compound

HRID 1197396Notes

Reaction equation

HRID 1197396 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].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.[C:22](=[O:25])([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=2[O:11][CH2:5][C:4]2[CH:8]=[CH:9][C:10]([O:25][CH3:22])=[CH:2][CH:3]=2)[C:5]([O:7][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[O:6])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 72Protocatechuic AcidHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 22419537HCID 22419537, compoundYield 125.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3,4-Dihydroxybenzoic acid (3.08 g, 0.02 mol) was dissolved in N,N-dimethylformamide (50 ml) and treated with 4-methoxybenzyl chloride (10 ml, 0.07 mol) and potassium carbonate (10 g, 0.07 mol). The mixture was warmed to 60° C. for 6 h and then stirred overnight. The mixture was partitioned between water and ethyl acetate. The organic phase was washed exhaustively with water and then the product was purified on silica gel 60 eluting with mixtures of ethyl acetate and hexane to give the title compound (6.48 g, 63%).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe organic phase was washed exhaustively with water
  3. customthe product was purified on silica gel 60 eluting with mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b7ce90c5d5354539b704ad684871d30a
Source dataset
uspto-grants-1994_01
Patent number
US05275816

Reaction notes

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