Acetic Acid → (4-Hydroxyimino-3-methoxy-cyclohexa-2,5-dienylidene)-phenylacetonitrile

HRID 612361

反応式

HRID 612361 の反応式
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=O.[OH-].[K+].C(O)(=O)C>CO.O>[OH:20][N:18]=[C:17]1[CH:16]=[CH:15][C:14](=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]#[N:9])[CH:13]=[C:12]1[O:11][CH3:10]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 70482-NitroanisoleHCID 8794PhenylacetonitrileHCID 14797Potassium Hydroxide

生成物 1

HCID 346837(4-Hydroxyimino-3-methoxy-cyclohexa-2,5-dienylidene)-phenylacetonitrile

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
55 °C

実験手順

21.0 g (0.18 mol) of phenylacetonitrile and 25 g (0.16 mol) of o-nitroanisole are added at 25° C. to a solution of 35.6 g KOH (0.54 mol, assay 85%) in 180 ml of methanol and the dark red reaction mixture is stirred at 55° C. for 6 hrs. After cooling, the mixture is diluted with 500 ml of water, and acidified by addition of 60 ml of acetic acid with cooling. The resulting orange precipitate is filtered, washed with water, methanol:water 1:1 (v/v), and dried at 80° C. under vacuum. The crude product (30.8 g, 75%) has a melting point of 180-182° C. (dec) (Lit: 187° C. dec; J. Org. Chem. 26, 4270, 1961) and is used in the next step without further purification. The 1H-NMR spectrum indicates the presence of two isomers in nearly 1:1 ratio.

後処理

  1. customthe dark red reaction mixture
  2. temperatureAfter cooling
  3. temperaturewith cooling
  4. filtrationThe resulting orange precipitate is filtered
  5. washwashed with water, methanol:water 1:1 (v/v)
  6. customdried at 80° C. under vacuum
  7. customis used in the next step without further purification

出典と根拠

ORDレコード
ord-a3f3c78cf1b146d4a3e0de8965e99580
出典データセット
uspto-grants-1999_12
特許番号
US06004724

関連ノート

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