4-Hydroxybenzoic Acid → 4-(Benzyloxy)benzoic acid

HRID 990021Notes

Reaction equation

HRID 990021 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+]>CN(C=O)C.O>[CH2:17]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 738804-(Benzyloxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzoic acid (6.9 g, 50 mmole) in 150 ml DMF was added potassium tert-butoxide (12.34 g, 110 mmole) and the mixture was stirred at room temperature for one hour. Benzyl bromide (20.5 g, 120 mmole) was added and the mixture was strred for two days at room temperature. The mixture was evaporated under reduced pressure and 100 ml 1,4-dioxane and a solution of sodium hydroxide (6.0 g, 150 mmole)in 50 ml water was added. The mixture was refluxed for two hours, cooled and evaporated under reduced pressure. Water was added and the mixture was acidified with acetic acid. The product was filtered, washed with cold water and dried. Yield: 10.2 g=89%.

Workup

  1. waitthe mixture was strred for two days at room temperature
  2. customThe mixture was evaporated under reduced pressure and 100 ml 1,4-dioxane
  3. temperatureThe mixture was refluxed for two hours
  4. temperaturecooled
  5. customevaporated under reduced pressure
  6. additionWater was added
  7. filtrationThe product was filtered
  8. washwashed with cold water
  9. customdried

Sources & evidence

ORD record
ord-bd85f75dc41f41818414df28f96847b0
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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