Butyl bromide → HCID 19809645, compound

HRID 374299Notes

Reaction equation

HRID 374299 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([CH3:16])=[CH:4][C:3]=1[OH:17].[CH2:18](Br)[CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:18]([O:17][C:3]1[CH:4]=[C:5]([CH3:16])[C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:7][C:2]=1[CH3:1])[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 19809653HCID 19809653, compound

Product 1

HCID 19809645HCID 19809645, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 13.4 g (59 mmol) of 2,5-dimethyl-4-(phenylmethoxy)phenol (Example K), 9.7 g (1.2×59 mmol) of butyl bromide and 12.2 g (1.5×59 mmol) of anhydrous potassium carbonate in 150 mL of acetonitrile is stirred at reflux for 40 hours. The reaction flask and inorganic residue are washed with acetonitrile and the filtrate is evaporated. Chromatography on a 3.5 cm column containing 175 g of basic alumina (activity grade I) prepared in 2:1 hexane-toluene and elution with the same solvent affords 13.1 g of the title compound; bp 153°-155° C./0.50 mm (mp 185°-195° C).

Workup

  1. temperatureat reflux for 40 hours
  2. washThe reaction flask and inorganic residue are washed with acetonitrile
  3. customthe filtrate is evaporated
  4. additionChromatography on a 3.5 cm column containing 175 g of basic alumina (activity grade I)
  5. customprepared in 2:1 hexane-toluene and elution with the same solvent

Sources & evidence

ORD record
ord-64097bbbdc8f4f1f90d9bfec4c10a544
Source dataset
uspto-grants-1992_11
Patent number
US05166398

Reaction notes

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