Hydrochloric Acid → 10-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid

HRID 1390562Notes

Reaction equation

HRID 1390562 reaction equation
[OH:1][C:2]1[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[CH:18]=[C:17]([CH3:25])[C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=O.C1(C)C=CC=CC=1.Cl>O>[OH:1][C:2]1[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[CH:18]=[C:17]([CH3:25])[C:3]=1[CH2:4][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 12906133HCID 12906133, compound

Product 1

HCID 1290613810-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9-(2'-Hydroxy-3',4'-dimethoxy-6'-methylbenzoyl)nonanoic acid (formula II-1, wherein R=H3CO, X=H, Y=OH, n=8, in the free form) (0.254 part), zinc amalgam (0.56 part), toluene (1 volume part), 35% hydrochloric acid (0.5 volume part) and a small proportion of water were refluxed for 5 hours. The toluene layer was separated and the water layer was extracted with diethyl ether. The toluene layer was combined with the ethereal layer, washed with water and dried. The solvents were then distilled off under reduced pressure and the residue was recrystallized from ligroine. The foregoing procedure provided 10-(2'-hydroxy-3',4'-dimethoxy-6'-methylphenyl)decanoic acid (formula II-2 wherein R=H3CO, X=H, n=8, in the free form) (0.14 part) as colorless powdery crystals melting at 62.5°-66° C.

Workup

  1. customThe toluene layer was separated
  2. extractionthe water layer was extracted with diethyl ether
  3. washwashed with water
  4. customdried
  5. distillationThe solvents were then distilled off under reduced pressure
  6. customthe residue was recrystallized from ligroine

Sources & evidence

ORD record
ord-bd8604a6787f40c79a75dabe63139290
Source dataset
uspto-grants-1979_02
Patent number
US04139545

Reaction notes

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