(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl butyrate → 2,3-Dihydroxypropyl butanoate

HRID 323900Notes

Reaction equation

HRID 323900 reaction equation
[C:1]([O:6][CH2:7][CH:8]1[CH2:12][O:11]C(C)(C)[O:9]1)(=[O:5])[CH2:2][CH2:3][CH3:4]>CO>[C:1]([O:6][CH2:7][CH:8]([OH:9])[CH2:12][OH:11])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 13498053(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl butyrate

Product 1

HCID 111882,3-Dihydroxypropyl butanoateYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 22 (50.6 g, 250 mmol), and Dowex 50W X8-100 H+ resin (76.5 g) in MeOH (500 ml), was heated at 50° C. for 2 hours, cooled to room temperature, filtered, and the resin washed with MeOH (1×200 ml). The methanol fractions were combined and concentrated in vacuo. The crude product was passed through a plug of silica gel using ethyl acetate:hexanes (1:1) as the eluent. Fractions containing the product were combined and concentrated in vacuo to afford 23 (32.8 g, 200 mmol, 81%) as an oil. The material was used in the next step without any further purification.

Workup

  1. filtrationfiltered
  2. washthe resin washed with MeOH (1×200 ml)
  3. concentrationconcentrated in vacuo
  4. additionFractions containing the product
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d30f8fb6b6e463eacc714ca1b4573e9
Source dataset
uspto-grants-2001_04
Patent number
US06215004B1

Reaction notes

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