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

HRID 33222ノート

反応式

HRID 33222 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  1. filtrationThe solid was filtered
  2. customthe filtrate evaporated

出典と根拠

ORDレコード
ord-6977855c72854170a3693e7676d59e38
出典データセット
uspto-grants-2008_09
特許番号
US07429579B2

反応ノート

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