1-Nonanol, 9-bromo- → 9-Phthalimidononan-1-ol

HRID 604531Notes

Reaction equation

HRID 604531 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[K].[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12>CN(C=O)C>[C:13]1(=[O:23])[N:17]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12

Participants

4

Reactant 2

HCID 1087001-Nonanol, 9-bromo-HCID 24194345Phthalimide potassium salt

Product 1

HCID 177695269-Phthalimidononan-1-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 9-bromononanol (Aldrich)(1.0 g, 4.5 mmol), phthalimide potassium derivative (1.85 g, 10 mmol) and DMF (10 ml) was heated at 100° C. for 1 hour. The mixture was allowed to cool to room temperature and was partitioned between ethyl acetate and water. The organic layer was washed with water, brine, dried over magnesium sulfate and evaporated under reduced pressure to afford the title compound as a white solid, 1.53 g, quantitative yield. m/z (LCMS ES+, 70 v) 290.1 (MH+), 312.1 (MNa+). δH (CHCl3-d) 7.81 (2H, m), 7.73 (2H, m), 3.64 (4H, m), 1.68 (2H, m), 1.59 (2H, m), 1.32 (10H, m). Intermediate 27

Workup

  1. temperatureto cool to room temperature
  2. customwas partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-542e2cd37fc14fd5b245914a99236dff
Source dataset
uspto-grants-2011_03
Patent number
US07910618B2

Reaction notes

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