Sodium Hydroxide → HCID 86652761, compound

HRID 453930Notes

Reaction equation

HRID 453930 reaction equation
[CH:1]1([O:6][C:7]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:18][OH:19].[OH-].[Na+]>C(O)C>[CH:1]1([O:6][C:7]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=[N:18][OH:19])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 6484666HCID 6484666, compound

Product 1

HCID 86652761HCID 86652761, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the stirred solution of 2-(cyclopentyloxy)-3-methoxybenzaldehyde (3 g, 13.636 mmol) in ethanol was added hydroxylamine hydrochloride (1.758 g, 27.277 mmol) and aqueous solution of sodium hydroxide (18 ml, 34.091 mmol). The reaction mixture was refluxed for 6 h under nitrogen atmosphere. The solvent was evaporated under reduced pressure and the reaction mixture diluted with water. The product was extracted using chloroform (3×200 ml), combined organic layers washed with water (3×100 ml), brine (50 ml), dried (Na2SO4), filtered and concentrated under vacuum to yield 3.12 g of the product. 1H NMR (300 MHz, CDCl3) δ 1.58-1.64 (m, 4H), 1.66-1.72 (m, 4H), 3.84 (s, 3H), 4.86 (br s, 1H), 6.89 (d, J=8.1 Hz, 1H), 6.99 (t, J=7.8 Hz, 1H), 7.31 (d, J=7.8 Hz, 1H), 8.43 (s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h under nitrogen atmosphere
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe reaction mixture diluted with water
  4. extractionThe product was extracted
  5. washwashed with water (3×100 ml), brine (50 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6d899aa9929c4ee39f4ebd274987225a
Source dataset
uspto-grants-2013_07
Patent number
US08492568B2

Reaction notes

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