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

HRID 647041Notes

Reaction equation

HRID 647041 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-4b6d210cd53b40b5b38d329f7bc3495c
Source dataset
uspto-grants-1983_10
Patent number
US04407757

Reaction notes

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