Hydroquinone → Methyl pyruvate

HRID 1590099Notes

Reaction equation

HRID 1590099 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[O:3].C(OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:26][O:27][C:28](OC)([CH3:33])[C:29]([O:31][CH3:32])=[O:30].C1(C=CC(O)=CC=1)O>CO>[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[O:3].[CH3:26][O:27][C:28](=[CH2:33])[C:29]([O:31][CH3:32])=[O:30]

Participants

8

Reactant 5

HCID 785HydroquinoneHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 11748Methyl pyruvateHCID 82339Methyl 2,2-dimethoxypropionate

Product 2

HCID 11748Methyl pyruvateHCID 536831Methyl 2-methoxyprop-2-enoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The dimethyl acetal of methyl pyruvate was prepared using methyl pyruvate, trimethyl orthoformate, MeOH and p-toluenesulfonic acid according to the method of Wermuth (Bull. Soc. Chim. France, 732 (1964)). Methyl pyruvate dimethylacetal (50 g) p-toluenesulfonic acid (1.34 g) and hydroquinone (1.90 g) were heated in an oil bath (approx. 150° C.) and MeOH was allowed to distill off slowly (approx. 10 mL). The residue was then distilled to afford the title ester, bp approx. 50° C./20 mmHg.

Workup

  1. distillationto distill off slowly (approx. 10 mL)
  2. distillationThe residue was then distilled

Sources & evidence

ORD record
ord-280d265466584b538b5f6f6dd376c3f1
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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