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

HRID 1757643Notes

Reaction equation

HRID 1757643 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>[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

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 24085Mercuric ChlorideCatalyst

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 tolueneand 220 ml of cone. 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. customToluene phase was separated
  2. customevaporated in vacuo
  3. customThe residue was crystallized from toluene-petroleum ether, yield 11.5 g (32%)

Sources & evidence

ORD record
ord-6dd749b1dbef45b0a87a1fc4a2d2fe04
Source dataset
uspto-grants-1995_08
Patent number
US05446194

Reaction notes

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