Benzaldehyde dimethyl acetal → 5-Methyl-2-phenyl-1,3-dioxane-5-carboxylic acid

HRID 1183128

Reaction equation

HRID 1183128 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4]([OH:6])=[O:5].CO[CH:12](OC)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:7][C:3]1([C:4]([OH:6])=[O:5])[CH2:8][O:9][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:1][CH2:2]1

Participants

5

Reactant 3

HCID 62375Benzaldehyde dimethyl acetalHCID 78501Dimethylolpropionic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 7047985-Methyl-2-phenyl-1,3-dioxane-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a round bottom flask was added sequentially 3-hydroxy-2-hydroxymethyl-2-methyl-propionic acid (10.0 g, 74.5 mmol), acetone (75.0 mL), benzaldehyde dimethyl acetal (17.02 g, 111.0 mmol) and para-toluenesulfonic acid monohydrate (0.71 g, 3.7 mmol). The resulting mixture was stirred at ambient temperature for 4 h and then filtered. The filter cake was rinsed with cold acetone and dried under vacuum to give the title compound as a white solid. 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.46-7.48 (m, 2H), 7.34-7.36 (m, 3H), 5.49 (s, 1H), 4.65 (d, J=10.8 Hz, 2H), 3.70 (d, J=11.4 Hz, 2H), 1.11 (s, 3H).

Workup

  1. filtrationfiltered
  2. washThe filter cake was rinsed with cold acetone
  3. customdried under vacuum

Sources & evidence

ORD record
ord-303086e98a164e7082f94a004ef3bc96
Source dataset
uspto-grants-2014_03
Patent number
US08664242B2

Linked notes

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