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

HRID 1722028

반응식

HRID 1722028 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8020Dimethoxymethane용매

반응 조건

온도
-70 °C

실험 절차

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.)

후처리

  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.)

출처 및 근거

ORD 기록
ord-15ad55d882074257918a81a38fc4eb73
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04853414

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