Sodium Hydroxide → HCID 22493735, compound

HRID 916880Notes

Reaction equation

HRID 916880 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, compoundYield 41.2%

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) was refluxed with stirring for 3 h. The reaction mixture was poured onto ice and made basic with 10 N NaOH and extracted with ether. The organic layer was washed with water, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane. To provide the desired compound as an oil (8.3 g, 41%); 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. temperaturewas refluxed
  2. additionThe reaction mixture was poured onto ice
  3. extractionextracted with ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a212b7a0585d4ca59889f1631db5b42d
Source dataset
uspto-grants-2007_09
Patent number
US07271270B2

Reaction notes

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