4-Toluenesulfonyl chloride → (2Z)-3-(2-cyanophenyl)prop-2-enoic acid

HRID 337153

反応式

HRID 337153 の反応式
[N:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13])=O.C1(C)C=CC(S(Cl)(=O)=[O:21])=CC=1.[OH-].[Na+]>C1COCC1.O>[C:3]([C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1/[CH:6]=[CH:5]\[C:4]([OH:13])=[O:21])#[N:1]

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 85801-Nitroso-2-naphtholHCID 14798Sodium Hydroxide

生成物 1

HCID 1899166(2Z)-3-(2-cyanophenyl)prop-2-enoic acid収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

A solution of 1-nitrosonaphthalen-2-ol (5 g) dissolved in THF (30 mL) was treated with p-toluenesulfonyl chloride (6.61 g) under nitrogen. The resulting mixture was stirred at 20° C. for 1 h. The mixture was treated with a solution of sodium hydroxide (4.04 g) in water (30 mL) dropwise over 30 min to keep temperature below 25° C. The reaction mixture was diluted with water (200 mL), and extracted with diethyl ether (200 mL) (discarded). The aqueous layer was acidified with 2M HCl, extracted with ethyl acetate (200 mL), dried (MgSO4), filtered and evaporated. The residue was triturated with 50% diethyl ether in isohexane to give the subtitle compound as a solid (4.75 g).

後処理

  1. customtemperature below 25° C
  2. extractionextracted with diethyl ether (200 mL) (discarded)
  3. extractionextracted with ethyl acetate (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with 50% diethyl ether in isohexane

出典と根拠

ORDレコード
ord-1becb3fd7a254e58af4cafa4c7829a00
出典データセット
uspto-grants-2014_11
特許番号
US08889692B2

関連ノート

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