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

HRID 1390565Notes

Reaction equation

HRID 1390565 reaction equation
[OH:1][C:2]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[C:18]([CH3:26])[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][CH3:17])=[O:15])=O.[H][H]>C(O)(=O)C.[Pd]>[OH:1][C:2]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[C:18]([CH3:26])[C:3]=1[CH2:4][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 2

HCID 12906141Methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)-10-oxodecanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 12824095Methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 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) (0.12 part) in acetic acid (17 volume parts) was shaken with 5% palladium-on-carbon in a current of hydrogen gas at 50°-60° C. The catalyst was removed by filtration and the acetic acid was distilled off under reduced pressure. The residue was subjected to column chromatography on silicic acid (6 parts) and elution was carried out with chloroform. The procedure provided methyl 10-(2'-hydroxy-3',4'-dimethoxy-6'-methylphenyl)decanoate (formula II-2 wherein R=H3CO, X=H, Y=OH, n=8, in the form of methyl ester) (0.09 part) as a colorless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe acetic acid was distilled off under reduced pressure
  3. washThe residue was subjected to column chromatography on silicic acid (6 parts) and elution

Sources & evidence

ORD record
ord-1945ce149aa64fa8ae3b996315d28f66
Source dataset
uspto-grants-1979_02
Patent number
US04139545

Reaction notes

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