Acetic Acid → HCID 12832660, compound

HRID 637909Notes

Reaction equation

HRID 637909 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 of 6-(18-hydroxy-1-oxooctadecyl)-2,3-dimethoxy-5-methylphenol (1.4 g) in acetic acid (30 ml) are added 5% palladium-on-carbon (50% hydrous) (0.5 g) and 70% perchloric acid (0.05 ml), and catalytic reduction is carried out at atmospheric temperature and pressure. After the absorption of hydrogen has subsided, the catalyst is filtered off and the filtrate is concentrated under reduced pressure, whereupon a colorless oil is obtained. This product is dissolved in ether and the ether layer is washed with 5% aqueous solution of sodium hydrogen carbonate and dried over anhydrous sodium sulfate. The solvent is then distilled off and the resultant crude crystals are recrystallized from hexane. The above procedure yields 6-(18-acetoxyoctadecyl)-2,3-dimethoxy-5-methylphenol (1.4 g) as colorless needles, m.p. 53° C.

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure, whereupon a colorless oil
  4. customis obtained
  5. washthe ether layer is washed with 5% aqueous solution of sodium hydrogen carbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent is then distilled off
  8. customthe resultant crude crystals are recrystallized from hexane

Sources & evidence

ORD record
ord-e4a5293ac6b2423fb2c81d77cdf7db69
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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