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

HRID 2108885ノート

反応式

HRID 2108885 の反応式
[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

参加物

8

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ddab9e05afdd475297bedf707f315db0
出典データセット
uspto-grants-2009_04
特許番号
US07514460B2

反応ノート

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