Acetic Acid → HCID 12832660, compound

HRID 1903433Notes

Reaction equation

HRID 1903433 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][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][C:19]([C:21]1[C:26]([OH:27])=[C:25]([O:28][CH3:29])[C:24]([O:30][CH3:31])=[CH:23][C:22]=1[CH3:32])=O.Cl(O)(=O)(=O)=O.[C:38](O)(=[O:40])[CH3:39]>CCOCC.[Pd]>[C:38]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][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][C:21]1[C:26]([OH:27])=[C:25]([O:28][CH3:29])[C:24]([O:30][CH3:31])=[CH:23][C:22]=1[CH3:32])(=[O:40])[CH3:39]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24247Perchloric AcidHCID 12832659HCID 12832659, compound

Product 1

HCID 12832660HCID 12832660, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution (30 ml) of 6-(18-hydroxy-1-oxooctadecyl)-2,3-dimethoxy-5-methylphenol (1.4 g) in acetic acid are added 5% palladium-on-carbon (50% hydrate; 0.5 g) and 70% perchloric acid (0.05 ml), and catalytic reduction is carried out at ambient temperature under atmospheric pressure. After completion of the absorption of hydrogen, the catalyst is filtered off and the filtrate is concentrated under reduced pressure to give a colorless oil. The oil is dissolved in ether, the ether layer is washed with a 5% aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate, and the solvent is distilled off to give crude crystals. Recrystallization from hexane gives colorless needles of 6-(18-acetoxyoctadecyl)-2,3-dimethoxy-5-methylphenol (1.4 g). m.p. 53° C.

Workup

  1. customis carried out at ambient temperature under atmospheric pressure
  2. customAfter completion of the absorption of hydrogen
  3. filtrationthe catalyst is filtered off
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customto give a colorless oil
  6. washthe ether layer is washed with a 5% aqueous sodium bicarbonate solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent is distilled off
  9. customto give crude crystals
  10. customRecrystallization from hexane

Sources & evidence

ORD record
ord-63b3898efeb640bf96323663f1315605
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

Loading…