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

HRID 988241노트

반응식

HRID 988241 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-74f3fbcdfc8c403eb5466523a4df711a
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06635655B1

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