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

HRID 714148

反応式

HRID 714148 の反応式
[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]

参加物

5

反応物 3

HCID 1183VanillinHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium Carbonate

生成物 1

HCID 796613-Methoxy-4-(methoxymethoxy)benzaldehyde収率 99.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-94d696110c384bc9991574215c3ef340
出典データセット
uspto-grants-2015_11
特許番号
US09187397B2

関連ノート

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