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

HRID 1248587Notes

Reaction equation

HRID 1248587 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, Y=OH, 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-6b4ea90ade3e4c2e8b863af747159d01
Source dataset
uspto-grants-1985_06
Patent number
US04525361

Reaction notes

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