2-Tert-Butylphenol → 7-(1,1-Dimethylethyl)-2,3-benzofurandione

HRID 2165095ノート

反応式

HRID 2165095 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:12](Cl)(=[O:16])[C:13](Cl)=[O:14].[Cl-].[Al+3].[Cl-].[Cl-]>CN(C)C1C=CN=CC=1.ClCCl.O.C(Cl)(Cl)Cl>[CH3:3][C:1]([C:5]1[C:6]2[O:11][C:13](=[O:14])[C:12](=[O:16])[C:7]=2[CH:8]=[CH:9][CH:10]=1)([CH3:4])[CH3:2]

参加物

8

反応物 3

HCID 69232-Tert-ButylphenolHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 122942517-(1,1-Dimethylethyl)-2,3-benzofurandione収率 47,987%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-tert-butylphenol (15 g, 0.1 mmol) and 4-dimethylaminopyridine (0.5 g) is stirred under nitrogen in 300 ml of dichloromethane. Oxalyl chloride (20 ml, 0.22 moles) is added dropwise, then the mixture is heated to reflux. After ten hours the mixture is cooled and the solvent is removed under reduced pressure. The residue is taken up in 100 ml of 1,2-dichloroethane and added dropwise under nitrogen to a suspension of aluminum chloride (40 g, 0.3 mmol) in 300 ml of 1,2-chloroethane. After 20 hours at room temperature the mixture is slowly diluted with water until all solids dissolve. The organic layer is separated and dried over molecular sieves, and the solvent is evaporated to leave a syrup which is taken up in chloroform and filtered through a short column of silica gel. The filtrate is stripped of solvent under reduced pressure to leave the product (9.8 g) as a syrup suitably pure for subsequent reactions.

後処理

  1. temperaturethe mixture is heated to reflux
  2. temperatureAfter ten hours the mixture is cooled
  3. customthe solvent is removed under reduced pressure
  4. dissolutiondissolve
  5. customThe organic layer is separated
  6. customdried over molecular sieves
  7. customthe solvent is evaporated
  8. customto leave a syrup which
  9. filtrationfiltered through a short column of silica gel

出典と根拠

ORDレコード
ord-7689778f11974050aeef94ec9a88b325
出典データセット
uspto-grants-1990_07
特許番号
US04939133

反応ノート

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