2,4-Dihydroxybenzoic Acid → HCID 9840634, compound

HRID 1814401Notes

Reaction equation

HRID 1814401 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:10]=[C:9]([O:11][CH2:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 14912,4-Dihydroxybenzoic AcidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 9840634HCID 9840634, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2,4-dihydroxybenzoic acid (5 g), anhydrous K2CO3 (40 g) and benzyl bromide (16 mL) in acetone (100 mL) was refluxed for 4 hours. After filtration of solid, the filtrate was concentrated. The residue was stirred at room temperature with KOH (6 g), and methanol (20 mL) for 4 hours, and neutralized with dilute HCl (pH 2). The solid thus formed was filtered and recrystallized from a methanol-chloroform mixture (3:1) to get 3.5 g of the product. Concentration of mother liquor gave an additional 1 g of the product.

Workup

  1. filtrationAfter filtration of solid
  2. concentrationthe filtrate was concentrated
  3. customThe solid thus formed
  4. filtrationwas filtered
  5. customrecrystallized from a methanol-chloroform mixture (3:1)

Sources & evidence

ORD record
ord-82a223264cd4458f87c41ef68cce7a73
Source dataset
uspto-grants-2005_04
Patent number
US06875882B2

Reaction notes

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