Methylparaben → Methyl 4-(4-phenylbutoxy)benzoate

HRID 52607

反応式

HRID 52607 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.C[O-].[Na+].[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>CN(C=O)C>[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 7456MethylparabenHCID 14798Sodium HydroxideHCID 2596681-Bromo-4-phenylbutaneHCID 10942334Sodium Methoxide

生成物 1

HCID 10978973Methyl 4-(4-phenylbutoxy)benzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

A solution of methyl 4-hydroxybenzoate (13.4 kg, 88 mol) in DMF (52 L) was added dropwise to a mixture of NaOMe (4.8 kg, 89 mol) and DMF (50 L) at room temperature under a gentle stream of nitrogen. The reaction mixture was heated at 60°-70° for 1 hr with stirring and then cooled to room temperature. To this mixture was added dropwise a solution of 4-phenylbutyl bromide (16.92 kg, 79.4 mol) in DMF (5 L). The resulting mixture was heated at 60°-70° for 1 hr with constant stirring and cooled to room temperature. After an addition of 1N-NaOH (110 L) was added, and the product was extracted twice with ethyl acetate (50 L and 80 L). The extracts were washed with 1N-NaOH (110 L) and saturated brine (20 L) successively, and then concentrated to dryness in vacuo to give the title compound in quantitative yield.

後処理

  1. temperatureThe reaction mixture was heated at 60°-70° for 1 hr
  2. temperatureThe resulting mixture was heated at 60°-70° for 1 hr
  3. stirringwith constant stirring
  4. temperaturecooled to room temperature
  5. additionwas added
  6. extractionthe product was extracted twice with ethyl acetate (50 L and 80 L)
  7. washThe extracts were washed with 1N-NaOH (110 L) and saturated brine (20 L) successively
  8. concentrationconcentrated to dryness in vacuo

出典と根拠

ORDレコード
ord-1459c7ee68434c8ab950324f3d1949b0
出典データセット
uspto-grants-1997_04
特許番号
US05616721

関連ノート

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