Sodium Carbonate → 4-Methoxy-3,5-dimethylbenzaldehyde oxime

HRID 1015950

反応式

HRID 1015950 の反応式
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[CH3:12].Cl.[NH2:14][OH:15].C([O-])([O-])=O.[Na+].[Na+]>C(O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:6]([CH:7]=[N:14][OH:15])=[CH:5][C:4]=1[CH3:12]

参加物

6

反応物 3

HCID 10340Sodium Carbonate2 回HCID 443297Hydroxyamine hydrochloride2 回HCID 27585734-Methoxy-3,5-dimethylbenzaldehyde

生成物 1

HCID 724690044-Methoxy-3,5-dimethylbenzaldehyde oxime収率 77%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

4-Methoxy-3,5-dimethylbenzaldehyde (1.86 g, 11.3 mmol) was dissolved in ethanol (30 mL) and stirred with hydroxylamine hydrochloride (2.4 M aq. solution, 5.65 mL, 1.2 eq.) and Na2CO3 (1.2 M solution, 5.65 mL, 0.6 eq.) at room temperature for 2.5 hours. The mixture was then heated to 60° C. and additional hydroxylamine hydrochloride and Na2CO3 was added. The mixture was again stirred overnight at 60° C., transferred to a separatory funnel, diluted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated. The product was purified by ISCO chromatography with EtOAc/hexanes eluent to yield 1.55 g (8.56 mmol, 77%) of 4-methoxy-3,5-dimethylbenzaldehyde oxime as a white solid. M+1=180.0.

後処理

  1. customtransferred to a separatory funnel
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by ISCO chromatography with EtOAc/hexanes eluent

出典と根拠

ORDレコード
ord-2f4de62927b24e1ba8be731fc7c664d6
出典データセット
uspto-grants-2011_07
特許番号
US07985762B2

関連ノート

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