p-Toluenesulfonic acid → HCID 14664466, compound

HRID 2298725Notes

Reaction equation

HRID 2298725 reaction equation
[OH:1][CH:2]([CH:7]([OH:16])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[C:17]1(C)[CH:22]=CC(S(O)(=O)=O)=C[CH:18]=1>S([O-])([O-])(=O)=O.[Cu+2].CC(C)=O>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]2[O:16][C:17]([CH3:22])([CH3:18])[O:1][CH:2]2[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13755108HCID 13755108, compound

Product 1

HCID 14664466HCID 14664466, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 180AcetoneSolvent

Procedure

Methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate (3.5 g, 15.5 mmol), copper sulphate anhydrous (4.3 g, 27 mmol, 1.8 equiv.) and acetone (40 ml, excess) were stirred in the presence of a catalytic amount of para-toluene sulphonic acid at 35° C. After 16 hours, the copper sulphate was removed by filtration, and the filtrate was removed and evaporated to dryness on a rotary evaporator. The product was purified by flash column chromatography using DCM as eluant. Evaporation of the appropriate fractions left methyl 5-(4-methoxyphenyl)-2,2-dimethyl -1,3-dioxolane 4-carboxylate as a clear, colourless oil (4.0 g, 96%). [a]D=+37.4° (THF, conc.=0.01712, 20° C). 1H-NMR was in accordance with expected signals.

Workup

  1. customthe copper sulphate was removed by filtration
  2. customthe filtrate was removed
  3. customevaporated to dryness on a rotary evaporator
  4. customThe product was purified by flash column chromatography
  5. customEvaporation of the appropriate fractions
  6. waitleft methyl 5-(4-methoxyphenyl)-2,2-dimethyl -1,3-dioxolane 4-carboxylate as a clear, colourless oil (4.0 g, 96%)
  7. custom[a]D=+37.4° (THF, conc.=0.01712, 20° C)

Sources & evidence

ORD record
ord-1b6c8536213745e2abf40417ede0c2a9
Source dataset
uspto-grants-2002_12
Patent number
US06495217B2

Reaction notes

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