Sodium Hydroxide → HCID 22493735, compound

HRID 1816416Notes

Reaction equation

HRID 1816416 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-75089e77d51b459497610a3b4a782ce4
Source dataset
uspto-grants-2005_04
Patent number
US06884815B1

Reaction notes

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