Hydrochloric Acid → Methyl 4-(cyanomethoxy)benzoate

HRID 1361021ノート

反応式

HRID 1361021 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]#[N:23].Cl>CC(C)=O.O>[C:22]([CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)#[N:23]

参加物

8

反応物 5

HCID 313Hydrochloric Acid2 回HCID 5238Sodium Iodide2 回HCID 7456MethylparabenHCID 7856Chloroacetonitrile3 回HCID 11430Potassium Carbonate2 回

生成物 1

HCID 594916Methyl 4-(cyanomethoxy)benzoate

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒2 回

実験手順

To a mixture of methyl 4-hydroxybenzoate (30.0 g, 0.20 mol), sodium iodide (30.0 g, 0.20 mol) and potassium carbonate (27.6 g, 0.20 mol) in acetone (2000 mL) was added chloroacetonitrile (14.9 g, 0.20 mol). The mixture was stirred at RT for 3 days. Water was added and the mixture was acidified with 1N hydrochloric acid and the mixture was extracted with diethyl ether. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in acetone and chloroacetonitrile (6.04 g, 0.08 mol), sodium iodide (12.0 g, 0.08 mol) and potassium carbonate (11.1 g, 0.08 mol) were added and the mixture was stirred for 16 hours at RT and at 60° C. More chloroacetonitrile was added until the conversion was 97%. Water was added and the mixture was acidified with 1N hydrochloric acid and the mixture was extracted with diethyl ether. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford methyl 4-cyanomethyloxybenzoate in quantitative yield. This compound was used without further purification in the following step.

後処理

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in acetone
  5. stirringthe mixture was stirred for 16 hours at RT and at 60° C
  6. extractionthe mixture was extracted with diethyl ether
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a30bb249df2e425ea668342edb258337
出典データセット
uspto-grants-2011_02
特許番号
US07879893B2

反応ノート

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