Butyl iodide → 6-Butoxy-3,3-dimethylindan-1-one

HRID 850025Notes

Reaction equation

HRID 850025 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:17][CH2:18][CH2:19][CH3:20]>CN(C=O)C>[CH2:17]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1)[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 193658996-Hydroxy-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 193659046-Butoxy-3,3-dimethylindan-1-oneYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under nitrogen, a solution of 28.5 g (0.16 mol) of 6-hydroxy-3,3-dimethylindan-1-one (J. Org. Chem. 19; 1954; 305) in 200 ml of DMF was added dropwise to a solution of 5.6 g (0.19 mol) of 80% sodium hydride in 250 ml of DMF. After 1 h at RT, 30.4 g (0.17 mol) of 1-iodobutane were added, and the mixture was stirred at RT for 2 h. The solvent was distilled off under reduced pressure, the residue was taken up in EA and water and the organic phase was washed successively with dil. hydrochloric acid and dil. sodium hydroxide solution. This procedure gave 31.3 g of 6-butoxy-3,3-dimethylindan-1-one.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. washwater and the organic phase was washed successively with dil. hydrochloric acid and dil. sodium hydroxide solution

Sources & evidence

ORD record
ord-a0c1447452e144df987603ea24fc4473
Source dataset
uspto-grants-2000_01
Patent number
US06015822

Reaction notes

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