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

HRID 68641

반응식

HRID 68641 반응식
[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

참가 물질

6

반응물 3

HCID 7456MethylparabenHCID 81051,5-PentanediolHCID 11776Triphenylphosphine

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 5462977Diethyl azodicarboxylate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a3818d1f2e964e4abb49da749142a5ba
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822459B2

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