Perchloric Acid → HCID 12824096, compound

HRID 1903423Notes

Reaction equation

HRID 1903423 reaction equation
[OH:1][C:2]1[C:33]([O:34][CH3:35])=[C:32]([O:36][CH3:37])[CH:31]=[C:30]([CH3:38])[C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=O.Cl(O)(=O)(=O)=O.[H][H]>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[C:33]([O:34][CH3:35])=[C:32]([O:36][CH3:37])[CH:31]=[C:30]([CH3:38])[C:3]=1[CH2:4][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]

Participants

6

Reactant 3

HCID 24247Perchloric AcidHCID 12824097Methyl 21-(2-hydroxy-3,4-dimethoxy-6-methylbenzoyl)heneicosanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 12824096HCID 12824096, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (15 ml) of 3 g of methyl 21-(2-hydroxy-3,4-dimethoxy-6-methylbenzoyl)heneicosanoate in ethyl acetate are added 0.015 ml of 60% perchloric acid and 600 mg of 5% palladium-on-carbon, and catalytic reduction is carried out at a 70° C. using hydrogen gas at the pressure of 100 kg/cm2. The catalyst is filtered off and the filtrate is washed in sequence with ice water, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. Removal of the solvent by distillation under reduced pressure gives colorless crystals of methyl 22-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)docosanoate. m.p. 71°-72.5° C.

Workup

  1. customis carried out at a 70° C.
  2. filtrationThe catalyst is filtered off
  3. washthe filtrate is washed in sequence with ice water
  4. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  5. customRemoval of the solvent
  6. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-2801014261f747fc8648c4c85a8b2301
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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