Sodium Hydroxide → HCID 22493735, compound

HRID 457353Notes

Reaction equation

HRID 457353 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-44d9a8184b524b778d23054820adb6c3
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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