Palmitic Acid → 2-Methyl-5-hexadecanoylhydroquinone

HRID 224470

Reaction equation

HRID 224470 reaction equation
B(F)(F)F.[C:5]([OH:22])(=O)[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][CH3:20].[CH3:23][C:24]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:25]=1[OH:26].C([O-])(=O)C.[Na+]>O.C(Cl)Cl>[CH3:23][C:24]1[CH:30]=[C:29]([OH:31])[C:28]([C:5](=[O:22])[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][CH3:20])=[CH:27][C:25]=1[OH:26]

Participants

7

Reactant 4

HCID 985Palmitic AcidHCID 6356Boron trifluorideHCID 7253MethylhydroquinoneHCID 517045Sodium Acetate

Product 1

HCID 147165312-Methyl-5-hexadecanoylhydroquinone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride was introduced with vigorous refluxing until saturation into a mixture of 27.2 g of palmitic acid, 13.7 g of 2-methylhydroquinone and 45 ml of methylene chloride. After standing overnight the mixture was refluxed for another hour and then decomposed with stirring in a solution of 25 g of sodium acetate in 220 ml of water. After 45 min the solution in methylene chloride was separated and evaporated. The residue was stirred with methanol, filtered with suction and recrystallized from n-chlorobutane.

Workup

  1. temperaturethe mixture was refluxed for another hour
  2. customAfter 45 min the solution in methylene chloride was separated
  3. customevaporated
  4. filtrationfiltered with suction
  5. customrecrystallized from n-chlorobutane

Sources & evidence

ORD record
ord-db9aa316efaf44f8a6f8972152474a09
Source dataset
uspto-grants-1980_11
Patent number
US04232107

Linked notes

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