m-Fluorotoluene → 2-Fluoro-4-methylbenzaldehyde

HRID 379353

반응식

HRID 379353 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1.FC1C=CC([CH:18]=[O:19])=C(C)C=1>Cl>[F:5][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][C:11]=1[CH:18]=[O:19]

참가 물질

5

반응물 3

HCID 9606m-FluorotolueneHCID 27832174-Fluoro-2-methylbenzaldehydeHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 27784712-Fluoro-4-methylbenzaldehyde수율 76.2%

시약·촉매·용매 1

HCID 313Hydrochloric Acid촉매

반응 조건

온도
60 °C

실험 절차

100.89 g of aluminum chloride (mol. Wt. 133.34; 756.6 mmol) and about 503.54 g of 3-fluorotoluene (mol. Wt. 110.13; 4,572 mmol) were charged to a 2 liter Parr®-brand 4522 stainless steel reaction vessel. To this mixture was added 5 drops of concentrated HCl. The vessel was sealed, heated to 60° C., and purged three times with carbon monoxide with the pressure of the vessel increased to 200 psi for each purging. After the third purge, the vessel was vented and a final introduction of CO was made at a pressure of about 200 psi, the pressure at which the reaction was maintained for the total reaction time of about 17 hours (the reaction temperature was maintained at 60° C. for the duration as well). Once the reaction was complete, the resultant mixture (exhibiting a dark orange color) was poured into about 500 mL of ice water (which turned the solution a yellow color), to which was added 500 mL of cyclohexane. The top, organic layer was removed and washed three times with water using a separatory funnel and dried over magnesium sulfate. The residual organic phase was then distilled under vacuum to remove excess cyclohexane, 3-fluorotoluene, and left about 79.65 g of a benzaldehyde mixture consisting of 4-fluoro-2-methylbenzaldehyde (88.4%) and 2-fluoro-4-methylbenzaldehyde (11.6%) (mol. Wt. 138.14; 576.6 mmol; yield of approximately 76.2%).

후처리

  1. customThe vessel was sealed
  2. custompurged three times with carbon monoxide with the pressure of the vessel
  3. temperatureincreased to 200 psi for each purging
  4. customAfter the third purge
  5. temperaturethe pressure at which the reaction was maintained for the total reaction time of about 17 hours (the reaction temperature
  6. temperaturewas maintained at 60° C. for the duration as well)
  7. additionwas poured into about 500 mL of ice water (which
  8. additionwas added 500 mL of cyclohexane
  9. customThe top, organic layer was removed
  10. washwashed three times with water using a separatory funnel
  11. dry with materialdried over magnesium sulfate
  12. distillationThe residual organic phase was then distilled under vacuum
  13. customto remove excess cyclohexane, 3-fluorotoluene
  14. waitleft about 79.65 g of a benzaldehyde mixture

출처 및 근거

ORD 기록
ord-eb1b066404544f7e92a16fdc26592af3
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297405B1

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