2,4-Dihydroxybenzoic Acid → HCID 9840634, compound

HRID 1761280Notes

Reaction equation

HRID 1761280 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].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH2:14]([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:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 14912,4-Dihydroxybenzoic AcidHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 9840634HCID 9840634, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-Dihydroxybenzoic acid was reacted with sodium hydride and benzyl bromide in dimethylformamide (DMF) to give a compound protected with benzyl groups at hydroxyl and carboxylic acids moieties in a 91% yield. The benzyl group was removed from the carboxylic acid moiety by refluxing it with 2 N sodium hydroxide in dioxane, followed by acidifying the mixture, to give 2,4-dibenzyloxybenzoic acid in 83% yield.

Workup

  1. customto give a compound
  2. customThe benzyl group was removed from the carboxylic acid moiety
  3. temperatureby refluxing it with 2 N sodium hydroxide in dioxane

Sources & evidence

ORD record
ord-7c2b8b3bcb0c4ea0a35513d13f7829d0
Source dataset
uspto-grants-2005_01
Patent number
US06846958B2

Reaction notes

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