p-Toluenesulfonic acid → Methyl 2-(2-formylphenyl)acetate

HRID 373953Notes

Reaction equation

HRID 373953 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11])=[O:2].[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 5289058Ortho-formylphenylacetic acid

Product 1

HCID 12241427Methyl 2-(2-formylphenyl)acetateYield 18,652%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

24.0 g (0.15 mole) of 2-formylphenylacetic acid and 0.1 g of p-toluenesulfonic acid in 250 ml of methanol are refluxed for 2 hours. Thereafter, the solution is evaporated down, the residue is taken up in diethyl ether and the solution is washed with dilute HCl. The organic phase is separated off, dried over MgSO4 and evaporated down. The residue is purified by distillation (90° C., 0.4 mbar). 19.3 g (74%) of methyl 2-formylphenylacetate are obtained as a colorless liquid in this manner.

Workup

  1. customThereafter, the solution is evaporated down
  2. washthe solution is washed with dilute HCl
  3. customThe organic phase is separated off
  4. dry with materialdried over MgSO4
  5. customevaporated down
  6. distillationThe residue is purified by distillation (90° C., 0.4 mbar)

Sources & evidence

ORD record
ord-618564f453c34b6b837166faab5ae121
Source dataset
uspto-grants-1992_11
Patent number
US05166216

Reaction notes

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