3-Hydroxybenzoic Acid → Benzyl 3-hydroxybenzoate

HRID 382381Notes

Reaction equation

HRID 382381 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:6]

Participants

5

Reactant 3

HCID 74203-Hydroxybenzoic AcidHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 11736317Benzyl 3-hydroxybenzoateYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.14 g (30 mmol) of 3-hydroxybenzoic acid was dissolved in 250 ml of N,N-dimethylformamide, and 2.49 g (18 mmol) of potassium carbonate and 3.8 ml (33 mmol) of benzyl chloride were added, followed by stirring at room temperature overnight. After the reaction solution was concentrated under vacuum, the residue was dissolved in ethyl acetate and 5% aqueous solution of sodium hydrogencarbonate. The organic layer was washed with 5% aqueous solution of sodium hydrogencarbonate, distilled water, and then with saturated brine, dried over anhydrous magnesium sulfate. This solution was concentrated under vacuum and the residue was crystallized from ethyl acetate-hexane to obtain 3.96 g of benzyl 3-hydroxybenzoate (yield 58%).

Workup

  1. concentrationAfter the reaction solution was concentrated under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with 5% aqueous solution of sodium hydrogencarbonate
  4. distillationdistilled water
  5. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  6. concentrationThis solution was concentrated under vacuum
  7. customthe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2876f8d1f3be4c47980c51ea50cd4b01
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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