p-Toluenesulfonic acid → Methyl 2-(2-methoxyethyl)-5-methyl-1,3-dioxane-5-carboxylate
Reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:12][CH2:13][C:14]([CH2:20][OH:21])([CH3:19])[C:15]([O:17][CH3:18])=[O:16].[CH3:22][O:23][CH:24](OC)[CH2:25][CH2:26]OC.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:22][O:23][CH2:24][CH2:25][CH:26]1[O:21][CH2:20][C:14]([CH3:19])([C:15]([O:17][CH3:18])=[O:16])[CH2:13][O:12]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
51 mg of 4-toluenesulphonic acid are added to a solution of 400 mg of methyl 3-hydroxyl-2-(hydroxymethyl)-2-methylpropanoate and 362 mg of 1,1,3-trimethoxypropane in toluene, and the mixture is stirred at 80° C. for 4 hours. After addition of saturated sodium bicarbonate solution, the organic phase is separated off and dried over sodium sulphate, and the solvent is removed under reduced pressure. The residue is filtered through silica gel (mobile phase cyclohexane/ethyl acetate 4:1). This gives 478 mg of methyl 2-(2-methoxyethyl)-5-methyl-1,3-dioxane-5-carboxylate as a mixture of two isomeric forms in a purity of about 38% (LCMS).
Workup
- customthe organic phase is separated off
- dry with materialdried over sodium sulphate
- customthe solvent is removed under reduced pressure
- filtrationThe residue is filtered through silica gel (mobile phase cyclohexane/ethyl acetate 4:1)
- additionThis gives 478 mg of methyl 2-(2-methoxyethyl)-5-methyl-1,3-dioxane-5-carboxylate as a mixture of two isomeric forms in a purity of about 38% (LCMS)
Sources & evidence
- ORD record
- ord-2d7f54ad89634a66a3c1b19286077fbd
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183351B2
Reaction notes
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