Methanesulfonic Acid → 2-Methyl-6-nitrochroman-4-one

HRID 1722041ノート

反応式

HRID 1722041 の反応式
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]([CH3:14])[CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[CH3:14][CH:9]1[CH2:10][C:11](=[O:13])[C:6]2[C:7](=[CH:15][CH:16]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[O:8]1

参加物

4

反応物 3

HCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)HCID 147733763-(4-Nitrophenoxy)butyric Acid

生成物 1

HCID 138500312-Methyl-6-nitrochroman-4-one

反応条件

温度
23 °C

実験手順

A mixture of 31.2 g (139 mmol) 3-(4-nitrophenoxy)butyric acid, 139 ml methanesulfonic acid and 7 g phosphorus pentoxide was heated on the steam bath for 1.75 hours. The reaction was cooled to 23° C., poured onto 500 ml ice-water mixture and extracted with 2×200 ml diethyl ether. The combined organic extracts were washed with 2×150 ml 1N sodium hydroxide, clarified by filtration, washed with 2×50 ml water and 100 ml brine, dried over magnesium sulfate and concentrated in vacuo to give the crude product as a yellow solid, 2.9 g (10%). Recrystallization from methylene chloride and isopropyl ether gave 1.35 g (4.7%) golden platelets, m.p. 144°-145° C.

後処理

  1. temperaturewas heated on the steam bath for 1.75 hours
  2. extractionextracted with 2×200 ml diethyl ether
  3. washThe combined organic extracts were washed with 2×150 ml 1N sodium hydroxide
  4. filtrationclarified by filtration
  5. washwashed with 2×50 ml water and 100 ml brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b06f5c113cc8494a80a1532f9623f239
出典データセット
uspto-grants-1989_08
特許番号
US04853410

反応ノート

読み込み中…