Carbon Dioxide → p-Toluic acid, 2,3,5,6-tetrafluoro-

HRID 1722028

反応式

HRID 1722028 の反応式
C([Li])CCC.[F:6][C:7]1[C:12]([F:13])=[CH:11][C:10]([F:14])=[C:9]([F:15])[C:8]=1[CH3:16].[C:17](=[O:19])=[O:18].Cl>COCOC.O>[CH3:16][C:8]1[C:7]([F:6])=[C:12]([F:13])[C:11]([C:17]([OH:19])=[O:18])=[C:10]([F:14])[C:9]=1[F:15]

参加物

7

反応物 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 788962,3,5,6-TetrafluorotolueneHCID 178418339Butyllithium

生成物 1

HCID 69548p-Toluic acid, 2,3,5,6-tetrafluoro-

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8020Dimethoxymethane溶媒

反応条件

温度
-70 °C

実験手順

A solution of n-butyllithium (2.7M in n-hexane, 21 cm3) was added dropwise to a stirred solution of 2,3,5,6-tetrafluorotoluene (9.0 g) in dry dimethoxymethane cooled to -70° C. under a nitrogen atmosphere and the mixture stirred for one hour. Carbon dioxide was then passed into the mixture for 3 hours during which time a white solid precipitate formed. After allowing the mixture to attain the ambient temperature (ca. 22° C.) it was poured into water. The resultant mixture was acidified with dilute hydrochloric acid and extracted with diethyl ether. The ethereal extract was washed with water and dried over anhydrous magnesium sulphate. Removal of the solvent yielded a semi solid residue which on trituration with petroleum ether (boiling range 40°-60° C.) gave 4-methyl-2,3,5,6-tetrafluorobenzoic acid (2.5 g) white crystals, mp 168° C. (Infra red C=O, 1700 cm-1.)

後処理

  1. customa white solid precipitate formed
  2. customthe ambient temperature (ca. 22° C.) it
  3. extractionextracted with diethyl ether
  4. extractionThe ethereal extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customRemoval of the solvent
  8. customyielded a semi solid residue which on trituration with petroleum ether (boiling range 40°-60° C.)

出典と根拠

ORDレコード
ord-15ad55d882074257918a81a38fc4eb73
出典データセット
uspto-grants-1989_08
特許番号
US04853414

関連ノート

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