Benzyl Bromide → Methyl 3-(benzyloxy)-4-methoxybenzoate

HRID 2108885노트

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HRID 2108885 반응식
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[C:14]([O:25][CH3:26])(=[O:24])[C:15]1[CH:23]=[CH:22][C:19]([O:20][CH3:21])=[C:17]([OH:18])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C)C=O.O>[CH2:14]([O:8][C:7]1[CH:9]=[CH:10][C:2]([C:1]([O:12][CH3:13])=[O:11])=[CH:3][C:4]=1[O:5][CH3:6])[C:15]1[CH:23]=[CH:22][CH:19]=[CH:17][CH:16]=1.[CH2:33]([O:18][C:17]1[CH:16]=[C:15]([CH:23]=[CH:22][C:19]=1[O:20][CH3:21])[C:14]([O:25][CH3:26])=[O:24])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

참가 물질

8

반응물 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19844Methyl VanillateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

생성물 2

HCID 4171221Methyl 3-(benzyloxy)-4-methoxybenzoateHCID 5059267Methyl 4-(benzyloxy)-3-methoxybenzoate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a solution of methyl vanillate or methyl isovanillate (7.29 g, 40 mmol) in dimethylformamide (25 mL), potassium carbonate (8.29 g, 60 mmol) and benzyl bromide (5.26 mL, 44 mmol) were added. The mixture was heated to 100° C. for 3 h. After cooling to r.t., water was added and the product was extracted several times with ethyl acetate. The combined organic phases were washed with water and brine. After drying over Na2SO4, the solvent was removed to yield methyl 4-benzyloxy-3-methoxybenzoate or methyl 3-benzyloxy-4-methoxybenzoate, respectively, quantitatively, which was used without further purification.

후처리

  1. temperatureAfter cooling to r.t.
  2. extractionthe product was extracted several times with ethyl acetate
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialAfter drying over Na2SO4
  5. customthe solvent was removed

출처 및 근거

ORD 기록
ord-ddab9e05afdd475297bedf707f315db0
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514460B2

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