Water → Ethyl 4-(benzyloxy)-2-hydroxy-6-methylbenzoate

HRID 2117194Notes

Reaction equation

HRID 2117194 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16].[OH2:21]>CC(C)=O>[CH2:19]([O:18][C:15](=[O:17])[C:16]1[C:13]([CH3:12])=[CH:8][C:9]([O:21][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:10][C:1]=1[OH:4])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 14408138Ethyl 4-(benzyloxy)-2-hydroxy-6-methylbenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl-2,4-dihydroxy-6-methyl benzoate (4 g, 21 mmol) is dissolved in acetone (80 mL) and to this solution is added potassium carbonate (2.9 g, 21 mmol) and benzyl bromide (2.5 mL, 21 mmol). This mixture is heated at reflux for 16 hours. To the cooled reaction is added ethyl acetate (100 mL) and water (100 mL). The organic layer is washed with water (2×80 mL) and brine (2×80 mL), then dried over magnesium sulfate and the solvent removed in vacuo. The crude is purified by column chromatography (silica, 10% ethyl acetate in hexanes) to give the title compound: 1H NMR (300 MHz, CDCl3) δ 7.38 (m, 5H), 6.41 (d, 1H), 6.38 (d, 1H), 5.05 (s, 2H), 4.40 (q, 2H), 2.51 (s, 3H), 1.40 (t, 3H).

Workup

  1. temperatureThis mixture is heated
  2. temperatureat reflux for 16 hours
  3. customTo the cooled reaction
  4. washThe organic layer is washed with water (2×80 mL) and brine (2×80 mL)
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent removed in vacuo
  7. customThe crude is purified by column chromatography (silica, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-869ce93216e84b46b627c096e3cde571
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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