Water → 2-(Benzyloxy)-3-methoxybenzaldehyde

HRID 413789

반응식

HRID 413789 반응식
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:13]([CH:14]=[O:15])[C:12]=1[OH:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[I-].[K+]>[CH2:1]([O:19][C:12]1[C:11]([O:10][CH3:9])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8991o-VanillinHCID 11430Potassium Carbonate

생성물 1

HCID 12680872-(Benzyloxy)-3-methoxybenzaldehyde수율 81%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

Benzyl bromide (8.6 ml) was added to a stirred solution of 3-methoxysalicylaldehyde (10 g), potassium carbonate (14.76 g) and potassium iodide (0.12 g) in DMF (120 ml) under an atmosphere of argon. The reaction was heated at 70° C. for 16 hours. Water (200 ml) was added causing the precipitation of a brown oil which crystallised on cooling. The solid was filtered, washed with water, dissolved in dichloromethane and dried (MgSO4). The solvent was removed in vacuo to give an oil which crystallised on trituration with iso-hexane to give the product as an off white solid (12.85 g, 81%); NMR d (CD3SOCD3) 3.91 (s, 3H), 5.15 (s, 2H), 7.14-7.22 (m, 2H), 7.29-7.42 (m, 6H), 10.10 (t, 1H); M/z (+) 243 (MH+).

후처리

  1. customthe precipitation of a brown oil which
  2. customcrystallised
  3. temperatureon cooling
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. dissolutiondissolved in dichloromethane
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customto give an oil which
  10. customcrystallised on trituration with iso-hexane

출처 및 근거

ORD 기록
ord-85cf6ef0ec784178b2581fde72b3ab84
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06569888B1

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