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

HRID 61639

反応式

HRID 61639 の反応式
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:6]([O:7][CH3:8])=[C:4]([OH:5])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.[Cl-].[Na+].O>[CH2:19]([O:5][C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][C:6]=1[O:7][CH3:8])[C:1]([O:12][CH2:1][C:2]1[CH:10]=[CH:9][CH:6]=[CH:4][CH:3]=1)=[O:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 3

HCID 7498Benzyl Bromide2 回HCID 11430Potassium CarbonateHCID 12575Isovanillic Acid

生成物 1

HCID 22070447Benzyl 3-(benzyloxy)-4-methoxybenzoate収率 180.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To an ice cold mixture of isovanillic acid 1 (4.3 g, 25.5 mmol) and K2CO3 (10.5 g, 0.152 mol) in anhydrous DMF (40 mL) was added benzyl bromide (8.7 g, 6.05 mL, 51.1 mmol). The resulting reaction mixture stirred at RT overnight. An additional aliquot of benzyl bromide was added (1.0 ml) and stirring was continued for 1.5 h. The reaction mixture was poured into brine (100 mL) and the solid was collected via filtration, washed with water and dried under high vacuum to give benzyl 3-(benzyloxy)-4-methoxybenzoate as a white solid (7.99 g, 23.0 mmol, 90%).

後処理

  1. customThe resulting reaction mixture
  2. stirringstirring
  3. waitwas continued for 1.5 h
  4. filtrationthe solid was collected via filtration
  5. washwashed with water
  6. customdried under high vacuum

出典と根拠

ORDレコード
ord-b8bb8dcd3c004e2d9534c17f0e7b911b
出典データセット
uspto-grants-2016_09
特許番号
US09440961B2

関連ノート

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