Hydrochloric Acid → HCID 9944111, compound

HRID 1797401Notes

Reaction equation

HRID 1797401 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[CH3:24])([CH3:14])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)=[O:6].Cl>[OH-].[Na+].CO>[CH3:14][C:4]([O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[CH3:24])([CH3:3])[CH:5]([C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[OH:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 9879261HCID 9879261, compound

Product 1

HCID 9944111HCID 9944111, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
35 °C

Procedure

A solution of sodium borohydride (25.7 g) in 0.1N NaOH (202 mL) was added dropwise to a suspension of 2-methyl-1-(4-methylphenyl)-2-(2,3,5-trimethylphenoxy)-1-propanone (251.9 g) in methanol (2519 mL). The mixture was stirred at 35° C. for 3 hours. After the mixture was adjusted to pH 7 by addition of 1N HCl under ice-cooling, methanol was distilled off, followed by extraction with toluene (2015 mL). The extract was washed with water, and the solvent was distilled off to quantitatively obtain the title compound as an oil (253.7 g).

Workup

  1. temperaturecooling
  2. distillationmethanol was distilled off
  3. extractionfollowed by extraction with toluene (2015 mL)
  4. washThe extract was washed with water
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-5a51473270354f18875136bc0acf72e4
Source dataset
uspto-grants-2006_04
Patent number
US07034166B2

Reaction notes

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