Hexamethylenetetramine → Methyl 4-formyl-3-methoxybenzoate

HRID 501811

反応式

HRID 501811 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7].BrN1C(=[O:20])CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C1N2CN3CN(C2)CN1C3>C1C=CC=CC=1.C(O)(=O)C.O>[CH:13]([C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1])=[O:20]

参加物

8

反応物 4

HCID 4101HexamethylenetetramineHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 591123Benzoic acid, 3-methoxy-4-methyl-, methyl ester

生成物 1

HCID 10631650Methyl 4-formyl-3-methoxybenzoate収率 64.6%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 241Benzene溶媒2 回HCID 962Water溶媒

実験手順

2.50 g of methyl 3-methoxy-4-methylbenzoate was dissolved in 25 mL of benzene, to which 2.72 g of N-bromosuccinimide and 0.23 g of 2,2′-azobisisobutyronitrile were successively added at room temperature, and this solution was stirred for one hour while heating it under reflux. After 3.90 g of hexamethylenetetramine dissolved in 7.8 mL of acetic acid and 7.8 mL of water was added dropwise to the reaction mixture, benzene was distilled out therefrom, and then the mixture was stirred for one hour while heating it under reflux. The reaction mixture, which was cooled to room temperature, was added to a mixture of chloroform and water and then adjusted to pH 7 with a 20% aqueous solution of sodium hydroxide, and the organic phase was separated therefrom. After the resultant organic phase was successively washed with water, a saturated aqueous solution of sodium hydrogen carbonate, and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1] to yield 1.74 g of methyl 4-formyl-3-methoxybenzoate as white solid.

後処理

  1. additionwere successively added at room temperature
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. distillationwas distilled out therefrom, and then the mixture
  5. stirringwas stirred for one hour
  6. temperaturewhile heating it
  7. temperatureunder reflux
  8. additionwas added to a mixture of chloroform and water
  9. customthe organic phase was separated
  10. washAfter the resultant organic phase was successively washed with water
  11. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled out under reduced pressure
  13. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1]

出典と根拠

ORDレコード
ord-a3ef6e1c4ac3432e90d3632acd088c9b
出典データセット
uspto-grants-2010_08
特許番号
US07772285B2

関連ノート

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