Benzyl Bromide → Methyl 4-benzyloxy-3-nitrobenzoate

HRID 1660803

反応式

HRID 1660803 の反応式
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

生成物 1

HCID 289857Methyl 4-benzyloxy-3-nitrobenzoate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of 4-hydroxy-3-nitro-benzoic acid methyl ester (30 g, 152 mmol) in acetone (1000 mL) was charged into a 2 L reactor and treated with K2CO3 (31.5 g, 228 mol) and benzyl bromide (52 g, 36.1 mL, 304 mmol). The mixture was mechanically stirred at heated at reflux for 16 hours under a light argon flux. After cooling to room temperature the solvent was evaporated. The residue was taken up in ethyl acetate/water and the two phases were separated. The aqueous phase was extracted three times with ethyl acetate (total solvent volume: 1.5 L, total water volume 1 L). The combined organic phases were dried over sodium sulfate and evaporated. 4-Benzyloxy-3-nitro-benzoic acid methyl ester thus obtained was used crude in the following reaction.

後処理

  1. temperatureat heated
  2. temperatureat reflux for 16 hours under a light argon flux
  3. customwas evaporated
  4. customthe two phases were separated
  5. extractionThe aqueous phase was extracted three times with ethyl acetate (total solvent volume: 1.5 L, total water volume 1 L)
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customevaporated

出典と根拠

ORDレコード
ord-7cddeaed8130442db8fbd55c3661e0c9
出典データセット
uspto-grants-2011_10
特許番号
US08030308B2

関連ノート

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