Vanillin → 3-Methoxy-4-(methoxymethoxy)benzaldehyde

HRID 714148노트

반응식

HRID 714148 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][CH2:20]Cl>CN(C)C=O>[CH3:18][O:19][CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11]

참가 물질

5

반응물 3

HCID 1183VanillinHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium Carbonate

생성물 1

HCID 796613-Methoxy-4-(methoxymethoxy)benzaldehyde수율 99.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Hydroxy-3-methoxybenzaldehyde (1a, 2.00 g, 13.1 mmol) and potassium carbonate (9.00 g, 65.1 mmol) were combined in dimethyl formamide (30 ml) and stirred for 15 min at room temperature. Chloromethyl methyl ether (1.60 ml, 21.1 mmol) was added and stirring was continued for 6 hr at room temperature. The resulting mixture was filtered and the filtrate extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to give 2.55 g (99%) of a white solid: mp 39-40° C. [expected mp 41° C.]; 1H NMR: δ 3.40 (s, 3H), 3.83 (s, 3H), 5.21 (s, 2H), 7.15 (d, 1H, J=8.7 Hz), 7.30 (dd, 1H, J=6.0, 2.0 Hz), 7.32 (s, 1H), 9.75 (s, 1H); 13C NMR: δ 55.8, 56.2, 94.8, 109.4, 114.6, 125.9, 130.9, 149.8, 151.7, 190.4.

후처리

  1. stirringstirring
  2. waitwas continued for 6 hr at room temperature
  3. filtrationThe resulting mixture was filtered
  4. extractionthe filtrate extracted into ethyl acetate
  5. washwashed with saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-94d696110c384bc9991574215c3ef340
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187397B2

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