Sulfuric Acid → 2-Phenoxyethyl 3-hydroxybenzoate

HRID 2220030Notes

Reaction equation

HRID 2220030 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[O:11]([CH2:18][CH2:19]O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.S(=O)(=O)(O)O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:19][CH2:18][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:6]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 74203-Hydroxybenzoic AcidHCID 31236Phenoxyethanol

Product 1

HCID 135053562-Phenoxyethyl 3-hydroxybenzoate

Conditions

Temperature
95 °C

Procedure

Into a 250 mL round bottom flask equipped with magnetic stirrer and heating mantle was added 16.0 parts of 3-hydroxy benzoic acid, 100 parts of 2-phenoxyethanol and 0.5 parts of concentrated sulfuric acid. The reaction mixture was heated at 95° C. for 48 hours. The excess of 2-phenoxyethanol was evaporated under reduced pressure at 90° C. The solid material was dissolved in 250 mL of ethyl acetate. The organic layer was first washed with 200 mL of water, second with 250 mL of 5% solution of sodium bicarbonate in water and finally washed with 3×250 mL of water. The ethyl acetate layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. This material was purified by chromatography on silica gel using 20% ethyl acetate/hexane. The desired fractions were combined and solvent was evaporated to give an oily material which on treatment with hexane gave a solid, yield 5.1 parts. TLC on silica gel plate showed single spot. The structure of the product was confirmed on the basis of 1H NMR. The reaction proceeded as follows:

Workup

  1. customInto a 250 mL round bottom flask equipped with magnetic stirrer
  2. temperatureheating mantle
  3. customThe excess of 2-phenoxyethanol was evaporated under reduced pressure at 90° C
  4. dissolutionThe solid material was dissolved in 250 mL of ethyl acetate
  5. washThe organic layer was first washed with 200 mL of water, second with 250 mL of 5% solution of sodium bicarbonate in water
  6. washfinally washed with 3×250 mL of water
  7. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThis material was purified by chromatography on silica gel using 20% ethyl acetate/hexane
  10. customsolvent was evaporated
  11. customto give an oily material which on treatment with hexane
  12. customgave a solid
  13. customyield 5.1 parts

Sources & evidence

ORD record
ord-e67268e14c5b41a2a072be29f9e5c28f
Source dataset
uspto-grants-2008_08
Patent number
US07416898B2

Reaction notes

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