Hydrochloric Acid → Ethyl [3-(benzyloxy)-4-hydroxyphenyl]acetate

HRID 5028Notes

Reaction equation

HRID 5028 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([OH:13])[CH:7]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>CC(C)=O.O>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15132249Ethyl 2-(3,4-dihydroxyphenyl)acetate

Product 1

HCID 54479398Ethyl [3-(benzyloxy)-4-hydroxyphenyl]acetateYield 45%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 5.79 g of 3,4-dihydroxylphenyl acetic acid ethyl ester dissolved in dry acetone were added 4.48 g of potassium carbonate and 4.15 ml of benzyl bromide. The mixture was heated to reflux until the starting materials were exhausted; and then the solvent was distilled off under reduced pressure. To the residues thus obtained was added 50 ml of water; and the mixture was acidified with concentrated hydrochloric acid and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to obtain residues, which were purified by chromatography to provide 3.80 g (yield 45%) of 3-benzyloxy-4-hydroxyphenylacetic acid ethyl ester, having the characteristics of: NMR(CDCl3, 200 MHz) δ1.24(t, J=7 Hz, 3H, CH3), 3.45(s, 2H, CH2CO), 4.12(q, J=7 Hz, 2H, OCH2), 5.05(s, 2H, CH2Ph), 6.77-7.35(m, 6H, ArH).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux until the starting materials
  3. distillationand then the solvent was distilled off under reduced pressure
  4. customTo the residues thus obtained
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customto obtain residues, which
  9. customwere purified by chromatography

Sources & evidence

ORD record
ord-102bee15751b4b71bb53e4792a6e7427
Source dataset
uspto-grants-1993_09
Patent number
US05242944

Reaction notes

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