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

HRID 1248588Notes

Reaction equation

HRID 1248588 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-f6b96eb8d6224770a415820d80d9e79c
Source dataset
uspto-grants-1985_06
Patent number
US04525361

Reaction notes

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