Vanillin → 4-(6-Bromo-hexanoyl)-3-methoxy-benzaldehyde

HRID 73507ノート

反応式

HRID 73507 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7].[O:8]=[CH:9][C:10]1[CH:18]=[CH:17][C:15](O)=[C:12]([O:13][CH3:14])[CH:11]=1.[C:19](=O)([O-])[O-:20].[K+].[K+]>CC(C)=O>[Br:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:19]([C:15]1[CH:17]=[CH:18][C:10]([CH:9]=[O:8])=[CH:11][C:12]=1[O:13][CH3:14])=[O:20]

参加物

5

反応物 3

HCID 1183VanillinHCID 81001,5-DibromopentaneHCID 11430Potassium Carbonate

生成物 1

HCID 866765364-(6-Bromo-hexanoyl)-3-methoxy-benzaldehyde収率 80%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

An excess of 1,5-dibromopentane (100 g, 3 equivalents) was added to a suspension of vanillin (43) (22 g) and potassium carbonate (30 g) in acetone (700 mL). The reaction mixture was heated at reflux for 2.5 hours and then allowed to stir at room temperature overnight, at which time TLC and LC/MS showed the reaction to be complete. The suspension was subjected to vacuum filtration and the resulting acetone solution was evaporated to dryness under reduced pressure. The residue was applied to a pad of silica gel and washed with 10% ethyl acetate in hexane (2 L) followed by 25% ethyl acetate in hexane to elute the product, removal of excess solvent by rotary evaporation under reduced pressure afforded the product 44 as an oil which crystallised on standing in freezer (35 g, 80% yield).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. customthe reaction
  4. filtrationThe suspension was subjected to vacuum filtration
  5. customthe resulting acetone solution was evaporated to dryness under reduced pressure
  6. washwashed with 10% ethyl acetate in hexane (2 L)
  7. washto elute
  8. customthe product, removal of excess solvent
  9. customby rotary evaporation under reduced pressure

出典と根拠

ORDレコード
ord-13f308e21ef74714b3722938d9ed1bcc
出典データセット
uspto-grants-2014_09
特許番号
US08829184B2

反応ノート

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