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

HRID 33222Notes

Reaction equation

HRID 33222 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  1. filtrationThe solid was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-6977855c72854170a3693e7676d59e38
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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