Hydrochloric Acid → 4-(2'-Hydroxy-3',4'-dimethoxy-6'-methylphenyl)butyric acid

HRID 1679844Notes

Reaction equation

HRID 1679844 reaction equation
[OH:1][C:2]1[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[C:11]([CH3:19])[C:3]=1[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=O.Cl.O>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[C:11]([CH3:19])[C:3]=1[CH2:4][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 129061353-(2'-Hydroxy-3',4'-dimethoxy-6'-methylbenzoyl)propionic acid

Product 1

HCID 129061404-(2'-Hydroxy-3',4'-dimethoxy-6'-methylphenyl)butyric acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(2'-hydroxy-3',4'-dimethoxy-6'-methylbenzoyl)propionic acid (formula II-1 wherein R=H3CO, X=H, Y=OH, n=2 in the free form) (0.536 part), zinc amalgam (1 part), concentrated hydrochloric acid (1 volume part), water (2 volume parts) and toluene (2 volume parts) was refluxed for 5 hours and, after cooling, the reaction mixture was extracted with diethyl ether. The extract was washed with water and dried. The solvents were distilled off under reduced pressure and the residue was recrystallized from diethyl ether-hexane. The procedure provided 4-(2'-hydroxy-3',4'-dimethoxy-6'-methylphenyl)butyric acid (formula II-2 wherein R=H3CO, X=H, Y=OH, n=2, in the free form) (0.34 part) as colorless needles melting at 98°-100° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureafter cooling
  3. extractionthe reaction mixture was extracted with diethyl ether
  4. washThe extract was washed with water
  5. customdried
  6. distillationThe solvents were distilled off under reduced pressure
  7. customthe residue was recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-af0429e446a24ccaa984859d30b17160
Source dataset
uspto-grants-1981_06
Patent number
US04271083

Reaction notes

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