Hydrochloric Acid → 6-(11-Hydroxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenol

HRID 1903427Notes

Reaction equation

HRID 1903427 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:17]1[C:22]([OH:23])=[C:21]([O:24][CH3:25])[C:20]([O:26][CH3:27])=[CH:19][C:18]=1[CH3:28])=[O:16])(=O)C.[OH-].[Na+].Cl>CO>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:17]1[C:22]([OH:23])=[C:21]([O:24][CH3:25])[C:20]([O:26][CH3:27])=[CH:19][C:18]=1[CH3:28])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 204311686-(11-Acetoxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenol

Product 1

HCID 132762366-(11-Hydroxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenolYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (300 ml) of 6-(11-acetoxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenol (34 g) in methanol is added sodium hydroxide (7 g), and the mixture is stirred at room temperature for 2 hours. After 5 N hydrochloric acid is added to the reaction mixture to neutralize, the solvent is distilled off to give crude crystals. The product is washed with water and recrystallized from ether-hexane (1:1) to give colorless needles of 6-(11-hydroxy-1-oxoundecyl)-2,3-dimethoxy-5-methyl-phenol (30 g). m.p. 81° C.

Workup

  1. distillationthe solvent is distilled off
  2. customto give crude crystals
  3. washThe product is washed with water
  4. customrecrystallized from ether-hexane (1:1)

Sources & evidence

ORD record
ord-3b0db15b099e4559a492892b5e405b5a
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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