Sodium Hydroxide → HCID 22493735, compound

HRID 1643187Notes

Reaction equation

HRID 1643187 reaction equation
Br[CH:2]([CH2:11][CH2:12][CH2:13][CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH:15]([O-:17])=O.[NH4+:18].[OH-].[Na+]>C(O)=O>[C:5]1([C:3]2[N:18]=[CH:15][O:17][C:2]=2[CH2:11][CH2:12][CH2:13][CH3:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723923Ammonium formateHCID 10611006HCID 10611006, compound

Product 1

HCID 22493735HCID 22493735, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of α-bromohexanophenone (25.5 g, 0.1 mole), ammonium formate (22 g, 0.35 mole) and formic acid (110 mL) is refluxed with stirring for 3 hours. The reaction mixture is poured onto ice, made basic with 10 N NaOH, and extracted with ether. The organic layer is washed with water, dried over sodium sulfate, and concentrated. The crude product is purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane to provide the desired compound as an oil. 1H NMR (δ, CDCl3, 400 MHz) 7.55 (m, 2H), 7.40 (s, 1H), 7.34 (dd, J=7,7 Hz, 2H), 7.22 (dd, J=7, 7 Hz, 1H), 2.74 (m, 2H), 1.6 (m, 2H), 1.30 (m, 2H), 0.84 (t, J=7 Hz, 3H) ppm.

Workup

  1. temperatureis refluxed
  2. additionThe reaction mixture is poured onto ice
  3. extractionextracted with ether
  4. washThe organic layer is washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-530b1f43488d4c5b9a9b86d88859faa8
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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