Hydrochloric Acid → 5-(3,4-dimethoxyphenyl)pentanoic acid

HRID 1195957Notes

Reaction equation

HRID 1195957 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl>[Zn].Cl[Hg]Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 27584705-(3,4-Dimethoxyphenyl)-5-oxovaleric acid

Product 1

HCID 2404595-(3,4-dimethoxyphenyl)pentanoic acid

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24085Mercuric ChlorideCatalystHCID 1140TolueneSolvent

Procedure

A mixture containing 37.6 g of the product obtained in Example 38 and 64 g of zinc turnings (treated with a solution of HgCl2), 55 ml of toluene and 220 ml of conc. hydrochloric acid was refluxed for 1 h. Toluene phase was separated and evaporated in vacuo. The residue was crystallized from toluene-petroleum ether, yield 11.5 g (32%).

Workup

  1. temperaturewas refluxed for 1 h
  2. customToluene phase was separated
  3. customevaporated in vacuo
  4. customThe residue was crystallized from toluene-petroleum ether, yield 11.5 g (32%)

Sources & evidence

ORD record
ord-2c8e13208b7e40e1b94f3ea51ea91a76
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

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