(1S)-(+)-Camphor-10-sulphonic acid → 3-methyl-1,4-Dioxane-2,5-dione

HRID 1491531Notes

Reaction equation

HRID 1491531 reaction equation
[C:1]([O:6][CH2:7][C:8]([O:10]C)=[O:9])(=[O:5])[CH:2]([CH3:4])O.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[CH3:4][CH:2]1[O:10][C:8](=[O:9])[CH2:7][O:6][C:1]1=[O:5]

Participants

4

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 197888162-Methoxy-2-oxoethyl lactate

Product 1

HCID 102908133-methyl-1,4-Dioxane-2,5-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

2-Methoxy-2-oxoethyl lactate (123 mg, 0.76 mmol), prepared as described in Example 1, was added to 25 mL of refluxing toluene containing (1S)-(+)-10-camphor-sulfonic acid (8.8 mg, 0.038 mmol). The refluxing toluene was made to pass through ca. 8 mL of crushed molecular sieves (type 4A) before returning to the reaction vessel. After 6 hr, the reaction mixture was cooled to room temperature, applied to a 40 mL silica gel column equilibrated in toluene and eluted with ethyl acetate. The ethyl acetate was evaporated and the title compound was identified as a component of the recovered material by GC (Method A) and GC/MS: HRMS calcd for C5H6O4 130.0266, obsd 130.0265.

Workup

  1. washeluted with ethyl acetate
  2. customThe ethyl acetate was evaporated

Sources & evidence

ORD record
ord-7f5c4b79d01a43389cb5d7e1114b7077
Source dataset
uspto-grants-1994_12
Patent number
US05371001

Reaction notes

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