Bromhydrol → HCID 14716731, compound

HRID 846552Notes

Reaction equation

HRID 846552 reaction equation
[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11]C)=[CH:7][CH:6]=1)=[O:4].[Br-].[Al+3].[Br-].[Br-]>C1(C)C=CC=CC=1>[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 166749BromhydrolHCID 54436508HCID 54436508, compound

Product 1

HCID 14716731HCID 14716731, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a flask of 50 m were charged 1.84 g (7.4 mmol) of 4-(2-methyloctanoyl) anisole and 35 ml of dried toluene, to which was added 8.68 g of anhydrous aluminum bromide under ice cooling with stirring, and further the stirring was continued at room temperature over a night. Thereafter, the reaction mixture was stirred at 40° C. for 4 hours, cooled to room temperature and poured into 100 ml of ice water. After the extraction with 40 ml of toluene twice, the organic layer was washed with 80 ml of water, dried on magnesium sulfate, filtered, concentrated and distilled under a reduced pressure to obtain 1.70 g (7.3 mmol, yield 98%) of a redish brown and oily (+)-4-(2-methyloctanoyl) phenol.

Workup

  1. waitfurther the stirring was continued at room temperature over a night
  2. stirringThereafter, the reaction mixture was stirred at 40° C. for 4 hours
  3. extractionAfter the extraction with 40 ml of toluene twice
  4. washthe organic layer was washed with 80 ml of water
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-31761682302749f1a40436eb714e2c60
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

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