p-Toluenesulfonic acid → 8,8,10-trimethyl-2H,8H-benzo[1,2-b;5,4-b']dipyran-2-one

HRID 1587053

反応式

HRID 1587053 の反応式
[CH3:1][C:2]1[C:3]([OH:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][C:9](=[O:12])[CH:8]=[CH:7]2.[CH3:14][C:15](O)([C:17]#[CH:18])[CH3:16].C1(C)C(C)=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:14][C:15]1([CH3:16])[O:13][C:3]2=[C:2]([CH3:1])[C:11]3[O:10][C:9](=[O:12])[CH:8]=[CH:7][C:6]=3[CH:5]=[C:4]2[CH:18]=[CH:17]1

参加物

5

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 7237O-XyleneHCID 82582-Methyl-3-butyn-2-olHCID 53809787-Hydroxy-8-methyl coumarin

生成物 1

HCID 131095828,8,10-trimethyl-2H,8H-benzo[1,2-b;5,4-b']dipyran-2-one収率 33%

実験手順

A solution prepared from 5.0 mmol of 8-methyl-7-hydroxycoumarin and 6.0 mmol of 2-methyl-3-butyn-2-ol in 40 ml of xylene containing 0.095 g (0.50 mmol) of p-toluenesulfonic acid was refluxed with magnetic stirring for 4 hours. The solvent was distilled off in vacuo and the oily contents of the flask chilled in an ice-salt water bath to induce crystallization. The white microneedles, 33% yield, were recrystallized from methanol to analytical purity, m.p. 105°-107° C. (lit. m.p. 106°-107° C.). The 1H-NMR spectrum was also identical to that reported, see P. Rodighiero et al., reference cited above.

後処理

  1. temperaturewas refluxed
  2. distillationThe solvent was distilled off in vacuo
  3. temperaturethe oily contents of the flask chilled in an ice-salt water bath
  4. customcrystallization
  5. customThe white microneedles, 33% yield, were recrystallized from methanol to analytical purity, m.p. 105°-107° C. (lit. m.p. 106°-107° C.)

出典と根拠

ORDレコード
ord-cfc078f11e9c459db970a3fad57e8112
出典データセット
uspto-grants-1993_06
特許番号
US05216176

関連ノート

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