Methanol → Methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)-10-oxodecanoate

HRID 1679845Notes

Reaction equation

HRID 1679845 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:5].[CH3:26]O>Cl>[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]([O:16][CH3:26])=[O:15])=[O:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 12906133HCID 12906133, compound

Product 1

HCID 12906141Methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)-10-oxodecanoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

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) (0.197 part) was dissolved in methanol saturated with hydrogen chloride gas (7 volume parts) and the solution was stirred at room temperature for 20 minutes. The methanol was distilled off under reduced pressure and the residue was recrystallized from hexane-diethyl ether. The procedure provided methyl 9-(2'-hydroxy-3',4'-dimethoxy-6'-methylbenzoyl)nonanoate (formula II-1 wherein R=H3CO, X=H, Y=OH, n=8, in the form of methyl ester) (0.195 part) as colorless needles melting at 49°-53° C.

Workup

  1. distillationThe methanol was distilled off under reduced pressure
  2. customthe residue was recrystallized from hexane-diethyl ether

Sources & evidence

ORD record
ord-2f72da9a7bb6431ab4df2507d3b65094
Source dataset
uspto-grants-1981_06
Patent number
US04271083

Reaction notes

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