Water → 5-Methyl-2,2-diphenyl-1,3-dioxane-5-carboxylic acid

HRID 406961

Reaction equation

HRID 406961 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4]([OH:6])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1.CO[C:23](OC)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C1(C)C=CC=CC=1>[CH3:7][C:3]1([C:4]([OH:6])=[O:5])[CH2:8][O:9][C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:1][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 752281,1'-(Dimethoxymethylene)bisbenzeneHCID 78501Dimethylolpropionic acid

Product 1

HCID 529317635-Methyl-2,2-diphenyl-1,3-dioxane-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
27.5 °C

Procedure

In a round bottom flask, (12 g) 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid and 35 ml toluene was taken. (99.4 mg) p-toluene sulfonic acid was added into the reaction mixture at 25-30° C. temperature. The reaction mixture was heated at reflux temperature, and 20.5 g (1 equiv.) dimethoxy diphenylmethane [IIa3] in 35 ml toluene was added and it was further refluxed under dean stark. Continuous removal and addition of toluene done upto 3 hrs. Then reaction mixture was cooled at 25-30° C. and dumped into water. The reaction mixture was stirred at 20-30° C. and filter it and wash the solid mass with water to obtain white solid product.

Workup

  1. temperatureThe reaction mixture was heated
  2. additionwas added
  3. temperatureit was further refluxed under dean stark
  4. customContinuous removal and addition of toluene
  5. customThen reaction mixture
  6. filtrationfilter it
  7. washwash the solid mass with water
  8. customto obtain white solid product

Sources & evidence

ORD record
ord-56938c7ac7b24dea9689b950922a301a
Source dataset
uspto-grants-2014_06
Patent number
US08754207B2

Linked notes

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