Diethyl Ether → 2-(2,4-Diethylbenzoyl)benzoic acid

HRID 55002

反応式

HRID 55002 の反応式
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH3:25])[CH:19]=1)[CH3:17].CCOCC>ClCC(Cl)(Cl)Cl>[CH2:16]([C:18]1[CH:19]=[C:20]([CH2:24][CH3:25])[CH:21]=[CH:22][C:23]=1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([OH:6])=[O:11])=[O:5])[CH3:17]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 6811Phthalic AnhydrideHCID 88641,3-DiethylbenzeneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 199571532-(2,4-Diethylbenzoyl)benzoic acid収率 93%

試薬・触媒・溶媒 1

HCID 124181,1,1,2-Tetrachloroethane溶媒2 回

実験手順

To a cooled mixture of phthalic anhydride (50 g, 0.34 mol) and aluminum chloride (99 g) in tetrachloroethane (300 mL) was added dropwise 1,3-diethylbenzene (50 g) over 11/4 hours. The mixture was stirred in an ice bath for 30 minutes, additional tetrachloroethane was added, and the mixture was stirred for 2 hours. The reaction mixture was poured into concentrated HCl/ice (1 L), ether (500 mL) was added and the mixture was filtered. The organic layer was separated, washed with saturated Na2CO3 (6×), the basic layer was extracted with CH2Cl2 and the CH2Cl2 layer was extracted with 2N NaOH and the 2N NaOH layer was acidified. The basic layer was acidified with aqueous HCl, this acidic layer was combined with the above acidified 2N NaOH layer and the mixture was extracted with ether. The CH2Cl2 layer and the ether layer were combined and concentrated in vacuo. The residue was slurried with water, filtered and rinsed with hexane to afford 88.8 g (93%) of 2-(2,4-diethylbenzoyl)benzoic acid, m.p. 115°-118° C.

後処理

  1. stirringthe mixture was stirred for 2 hours
  2. additionwas added
  3. filtrationthe mixture was filtered
  4. customThe organic layer was separated
  5. washwashed with saturated Na2CO3 (6×)
  6. extractionthe basic layer was extracted with CH2Cl2
  7. extractionthe CH2Cl2 layer was extracted with 2N NaOH
  8. extractionthe mixture was extracted with ether
  9. concentrationconcentrated in vacuo
  10. filtrationfiltered
  11. washrinsed with hexane

出典と根拠

ORDレコード
ord-6cc04374b2914c638e36d02d78689a42
出典データセット
uspto-grants-1997_04
特許番号
US05624922

関連ノート

読み込み中…