Methylparaben → Methyl 4-((5-hydroxypentyl)oxy)benzoate

HRID 68641

反応式

HRID 68641 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].[CH2:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][OH:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CCOC(/N=N/C(OCC)=O)=O>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 7456MethylparabenHCID 81051,5-PentanediolHCID 11776Triphenylphosphine

生成物 1

HCID 65019122Methyl 4-((5-hydroxypentyl)oxy)benzoate収率 68%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 5462977Diethyl azodicarboxylate溶媒

実験手順

To a solution of methyl p-hydroxybenzoate (3.38 g), 1,5-pentanediol (2.30 g) and triphenylphosphine (5.96 g) in tetrahydrofuran (100 mL), diethylazodicarboxylate (2.2N toluene solution, 10 mL) was slowly added under ice cooling. The reaction mixture was stirred under ice cooling for 16 hours. The reaction mixture was concentrated and the residue was washed with n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1). The reaction mixture was concentrated and then purified by silica gel chromatography (n-hexane:ethyl acetate=64:36→45:55) to obtain the title compound (3.58 g) having the following physical properties.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1)
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by silica gel chromatography (n-hexane:ethyl acetate=64:36→45:55)

出典と根拠

ORDレコード
ord-a3818d1f2e964e4abb49da749142a5ba
出典データセット
uspto-grants-2014_09
特許番号
US08822459B2

関連ノート

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