Dimethylolpropionic acid → HCID 14530206, compound

HRID 1436898Notes

Reaction equation

HRID 1436898 reaction equation
OC[C:3]([CH2:8][OH:9])([CH3:7])[C:4]([OH:6])=[O:5].[OH2:10].[C:11]1([CH3:21])C=CC(S(O)(=O)=O)=C[CH:12]=1>>[CH3:12][C:11]1([CH3:21])[O:9][CH2:8][C:3]([CH3:7])([C:4]([OH:6])=[O:5])[O:10]1

Participants

3

Reactant 2

HCID 78501Dimethylolpropionic acidHCID 521998p-Toluenesulfonic acid monohydrate2×

Product 1

HCID 14530206HCID 14530206, compoundYield 416.3%

Procedure

To 1.34 g of 3-hydroxyl-2-hydroxymethyl-2-methylpropionic acid and 13 ml of acetonedimethylacetal was added 95 mg of p-toluenesulfonic acid monohydrate at room temperature, and the mixture was stirred for 6 hours. Further added thereto was 95 mg of p-toluenesulfonic acid monohydrate, and the mixture was stirred overnight. The solution was concentrated and poured into water and extracted. The aqueous layer was extracted with chloroform. The combined organic layers were washed with saturated brine, dried, and concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol=19:1), to give 333 mg of 2,2,5-trimethyl-[1,3]dioxolane-5-carboxylic acid as shown in Table 132 below.

Workup

  1. additionFurther added
  2. stirringthe mixture was stirred overnight
  3. concentrationThe solution was concentrated
  4. additionpoured into water
  5. extractionextracted
  6. extractionThe aqueous layer was extracted with chloroform
  7. washThe combined organic layers were washed with saturated brine
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-f1f7051ff98241ff8b249c02e8e53bdc
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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