Bromhydrol → HCID 14716731, compound

HRID 2372245Notes

Reaction equation

HRID 2372245 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 98.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a flask of 50 ml were charged 1.84 g (7.4 mmol) of the above 4-(2-methyloctanoyl) anisole and 35 ml of dried toluene, and 8.68 g of anhydrous aluminum bromide was added thereto with stirring under ice cooling, which were then stirred at room temperature over a night. Thereafter, the mixture was stirred at 40° C. for 4 hours, air cooled and poured into 100 ml of ice water. After the extraction with 40 ml of toluene was repeated two times, the organic layer was washed with 80 ml of water and dried on magnesium sulfate. After the filtration and concentration, the product was dried under a reduced pressure to obtain 1.70 g (7.3 mmol, yield: 98%) of a reddish brown oily (+)-4-(2-methyloctanoyl) phenol having the following properties:

Workup

  1. additionwas added
  2. stirringwhich were then stirred at room temperature over a night
  3. stirringThereafter, the mixture was stirred at 40° C. for 4 hours
  4. temperatureair cooled
  5. extractionAfter the extraction with 40 ml of toluene
  6. washthe organic layer was washed with 80 ml of water
  7. customdried on magnesium sulfate
  8. filtrationAfter the filtration and concentration
  9. customthe product was dried under a reduced pressure

Sources & evidence

ORD record
ord-d41b2d894a5e4eae871a133176bf3f67
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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