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

HRID 1697411

반응식

HRID 1697411 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-89af74b318084a77bf1c6fd3797eb7ad
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163905B2

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