p-Toluenesulfonic acid → 2-((4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

HRID 561231Notes

Reaction equation

HRID 561231 reaction equation
[CH2:1]([C:7]([OH:9])=[O:8])[C@@H:2]([OH:6])[C:3]([OH:5])=[O:4].CO[C:12](OC)([CH3:14])[CH3:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH3:13][C:12]1([CH3:14])[O:6][C@H:2]([CH2:1][C:7]([OH:9])=[O:8])[C:3](=[O:5])[O:4]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 92824D-Malic acid

Product 1

HCID 108449602-((4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of D-(+)-malic acid (10 g, 75 mmol) in CH2Cl2 (100 mL) was added 2,2-dimethoxypropane (23 g, 225 mmol) and p-toluenesulfonic acid (0.129 g, 0.75 mmol). The reaction mixture was stirred at rt for 4 h, filtered through silica gel (50% EtOAc/hexane) and concentrated to give the title compound.

Workup

  1. filtrationfiltered through silica gel (50% EtOAc/hexane)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9dddeacd5c7d4874a38679e1123166e0
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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