Hydrochloric Acid → Methyl 3-(4-formylphenyl)propanoate

HRID 986551Notes

Reaction equation

HRID 986551 reaction equation
Cl.C1COO[C:5]([O:16][CH3:17])([CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=2)[O:4]O1>O1CCCC1>[CH:14]([C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][C:5]([O:16][CH3:17])=[O:4])=[CH:9][CH:10]=1)=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86741942Methyl 3-(4-formylphenyl)propanoate ethylenedioxy acetal

Product 1

HCID 11063253Methyl 3-(4-formylphenyl)propanoateYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1M Hydrochloric acid (182 ml) was added to a stirred solution of methyl 3-(4-formylphenyl)propanoate ethylenedioxy acetal (16 g, 68 mmole, from example 33) in tetrahydrofuran (1100 ml) at 0° C. and the mixture stirred overnight at room temperature. The acid was neutralised and the product was extracted into ether. Evaporation of the dried (MgSO4) extracts gave 10.54 g (81%) of the title compound as an oil, νmax (film) 1735, 1700, 1605 cm-1, which was used without further purification.

Workup

  1. extractionthe product was extracted into ether
  2. customEvaporation of the
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-ddcfec2ce41749259de932b3eb2f806d
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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