Water → HCID 131735413, compound

HRID 630647Notes

Reaction equation

HRID 630647 reaction equation
[CH2:1]([C:5]1([CH2:21][CH2:22][CH2:23][CH3:24])[C:17]2[CH:16]=[C:15]([C:18](=O)[CH3:19])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH3:4].Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:1]([C:5]1([CH2:21][CH2:22][CH2:23][CH3:24])[C:17]2[CH:16]=[C:15]([C:18](=[N:26][OH:27])[CH3:19])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86237345HCID 86237345, compound

Product 1

HCID 131735413HCID 131735413, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After 5.45 g of 1-(9,9-di-n-butylfluorene-2-yl)-ethanone (12) (17 mmol) was dispersed in 50 ml of ethanol and 1.42 g of hydroxylamine hydrochloride (20.4 mmol) and 1.67 g of sodium acetate (20.4 mmol) were added thereto, the reaction mixture was slowly heated and refluxed for 1 hour. The reaction mixture was cooled to room temperature, and 100 ml of distilled water was added thereto and stirred for about 30 minutes. Then, the product was extracted with 200 ml of ethylacetate and sequentially washed with saturated aqueous sodium bicarbonate solution and 100 ml of distilled water, and the recovered organic layer was dried over anhydrous magnesium sulfate, followed by distilling the solvent under reduced pressure. The obtained solid product was dried, thereby obtaining 4.97 g of 1-(9,9-di-n-butylfluorene-2-yl)-ethanone oxime (13) (87.3%) as a light yellow product.

Workup

  1. temperaturethe reaction mixture was slowly heated
  2. temperaturerefluxed for 1 hour
  3. extractionThen, the product was extracted with 200 ml of ethylacetate
  4. washsequentially washed with saturated aqueous sodium bicarbonate solution and 100 ml of distilled water
  5. dry with materialthe recovered organic layer was dried over anhydrous magnesium sulfate
  6. distillationby distilling the solvent under reduced pressure
  7. customThe obtained solid product was dried

Sources & evidence

ORD record
ord-8681bc6baa6f4246845ad27e75fb29a5
Source dataset
uspto-grants-2016_04
Patent number
US09316906B2

Reaction notes

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