Butyl iodide → 6-Butoxy-2,2-dimethylchroman-4-one

HRID 618821Notes

Reaction equation

HRID 618821 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:13])[CH:8]=2)[O:3]1.[H-].[Na+].I[CH2:18][CH2:19][CH2:20][CH3:21]>CN(C=O)C>[CH2:18]([O:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:14])([CH3:1])[CH2:11][C:10]2=[O:12])[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 35198596-Hydroxy-2,2-dimethylchroman-4-one

Product 1

HCID 110540056-Butoxy-2,2-dimethylchroman-4-oneYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 50 g (0.26 mol) of 2,2-dimethyl-6-hydroxychroman-4-one (Example 28a) in 500 ml of DMF was added dropwise to a suspension of 9.0 g (0.3 mol) of 80% sodium hydride in 500 ml of DMF. After stirring at RT for 90 min, 49 g (0.265 mol) of iodobutane were added and the mixture was stirred at RT for a further 90 min. The reaction mixture was then concentrated in vacuo, the residue was treated with water and the mixture was extracted several times with EA. The organic phases were washed with 5 M sodium hydroxide solution, stirred with activated carbon and magnesium sulfate, filtered and concentrated. 57.6 g of 6-butoxy-2,2-dimethylchroman-4-one were obtained.

Workup

  1. stirringthe mixture was stirred at RT for a further 90 min
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. additionthe residue was treated with water
  4. extractionthe mixture was extracted several times with EA
  5. washThe organic phases were washed with 5 M sodium hydroxide solution
  6. stirringstirred with activated carbon and magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0e426e1ddffc4afd8e0fc805161a3a1d
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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