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

HRID 1808501노트

반응식

HRID 1808501 반응식
[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

참가 물질

6

반응물 3

HCID 7498Benzyl Bromide2회HCID 11430Potassium CarbonateHCID 12575Isovanillic Acid

생성물 1

HCID 22070447Benzyl 3-(benzyloxy)-4-methoxybenzoate수율 180.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-52d001bf655849ca8a7feb9871c9a7d6
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357693B2

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