1,2-Dichlorobenzene → 2,4-Dimethyl-3-fluorobenzaldehyde

HRID 379354

反応式

HRID 379354 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1Cl.[F:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21].FC1C(C)=CC([CH:27]=[O:28])=CC=1C>Cl>[F:13][C:14]1[C:19]([CH3:20])=[C:18]([CH:17]=[CH:16][C:15]=1[CH3:21])[CH:27]=[O:28]

参加物

6

反応物 4

HCID 72391,2-DichlorobenzeneHCID 1230652-Fluoro-m-xyleneHCID 6451240Aluminum(III) ChlorideHCID 120407104-Fluoro-3,5-dimethylbenzaldehyde

生成物 1

HCID 120407112,4-Dimethyl-3-fluorobenzaldehyde収率 68.6%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid触媒

反応条件

温度
50 °C

実験手順

62.4 g of aluminum chloride (mol. Wt. 133.34; 468.0 mmol), 450.0 g of 1,2-dichlorobenzene (mol. Wt. 147.00; 3,061 mmol), and about 48.00 g of 2-fluoro-m-xylene (mol. Wt. 124.16; 386.6 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 50° C., and purged three times with carbon monoxide with the pressure of the vessel increased to 100 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 16 hours (the reaction temperature was maintained at 50° 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, 2-fluoro-m-xylene, 1,2-dichlorobenzene, and left about 40.39 g of a benzaldehyde mixture consisting of 4-fluoro-3,5-dimethylbenzaldehyde (73.8%) and 3-fluoro-2,4-dimethylbenzaldehyde (26.2%) (mol. Wt. 152.17; 265.4 mmol; yield of approximately 68.6%).

後処理

  1. customThe vessel was sealed
  2. custompurged three times with carbon monoxide with the pressure of the vessel
  3. temperatureincreased to 100 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 16 hours (the reaction temperature
  6. temperaturewas maintained at 50° 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, 2-fluoro-m-xylene, 1,2-dichlorobenzene
  14. waitleft about 40.39 g of a benzaldehyde mixture

出典と根拠

ORDレコード
ord-c140254512cb4da989544a7a9e8425fc
出典データセット
uspto-grants-2001_10
特許番号
US06297405B1

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