p-Toluenesulfonic acid → 4-[1,3]Dioxan-2-yl-butyric acid methyl ester

HRID 33222노트

반응식

HRID 33222 반응식
[CH3:1][O:2][CH:3]([O:11][CH3:12])[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[CH2:13](O)CCO.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:10][O:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]1[O:11][CH2:12][CH2:13][CH2:1][O:2]1

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 516892Sodium BicarbonateHCID 551444Methyl 5,5-dimethoxyvalerate

생성물 1

HCID 693128054-[1,3]Dioxan-2-yl-butyric acid methyl ester수율 103.9%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

Methyl 5,5-dimethoxyvalerate (20.0 g, 0.114 mol), propane-1,3-diol (13 g, 0.17 mol) and para-toluene sulphonic acid (2.17 g, 0.0114 mol) were heated under Dean-Stark conditions in toluene (100 ml) for 4 h. The mixture was cooled to room temperature and diluted with diethyl ether (100 ml) and then neutralized with solid sodium bicarbonate. The solid was filtered and the filtrate evaporated to give a pale yellow oil (22.3 g). A 10 g portion of this was then purified by silica gel chromatography (eluent 30% EtOAc:hexane) which gave the title compound as a colourless oil (6.82 g).

후처리

  1. filtrationThe solid was filtered
  2. customthe filtrate evaporated

출처 및 근거

ORD 기록
ord-6977855c72854170a3693e7676d59e38
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429579B2

반응 노트

불러오는 중…