Oxygen → 2-Chlorobenzoic Acid

HRID 258594

반응식

HRID 258594 반응식
Cl[C:2]1C=C[CH:5]=[CH:4][C:3]=1C.[CH2:9]([CH:11]1[O:13][CH2:12]1)[Cl:10].[O:14]=O>CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Co+2]>[Cl:10][C:9]1[CH:5]=[CH:4][CH:3]=[CH:2][C:11]=1[C:12]([OH:13])=[O:14]

참가 물질

5

반응물 3

HCID 977OxygenHCID 72382-ChlorotolueneHCID 7835Epichlorohydrin

생성물 1

HCID 83742-Chlorobenzoic Acid

시약·촉매·용매 1

HCID 8696Cobalt octoate촉매

반응 조건

온도
155 °C

실험 절차

Into the column were charged 453 grams (3.58 moles) of o-chlorotoluene, 2.25 grams of cobalt octoate (6% Co), and 1.0 gram of epichlorohydrin. The reaction mixture was heated to 155° C. and maintained at that temperature while oxygen was bubbled through it at the rate of 300 ml./min. An additional 1.0 gram of epichlorohydrin was added to the reaction mixture every two hours during the oxidation. Throughout the reaction period, the gases leaving the column remained non-acidic. At the end of 14 hours, when 35 grams of water had been collected, the reaction mixture was removed from the column, cooled to 75° C. and extracted with 600 grams of 10 percent aqueous sodium hydroxide solution. The layers that formed were separated. The aqueous layer was diluted with water to a volume of 1500 ml. and then acidified with hydrochloric acid. The o-chlorobenzoic acid that precipitated was collected, washed with water, and dried. There was obtained 177 grams (1.135 moles) of o-chlorobenzoic acid. The conversion of o-chlorotoluene to o-chlorobenzoic acid was 43 percent. The yield of o-chlorobenzoic acid, based on o-chlorotoluene reacted, was 73.8 percent.

후처리

  1. customwas bubbled through it at the rate of 300 ml
  2. additionAn additional 1.0 gram of epichlorohydrin was added to the reaction mixture every two hours during the oxidation
  3. customThroughout the reaction period
  4. customthe gases leaving the column
  5. customAt the end of 14 hours, when 35 grams of water had been collected
  6. customthe reaction mixture was removed from the column
  7. temperaturecooled to 75° C.
  8. extractionextracted with 600 grams of 10 percent aqueous sodium hydroxide solution
  9. customThe layers that formed
  10. customwere separated
  11. additionThe aqueous layer was diluted with water to a volume of 1500 ml
  12. customThe o-chlorobenzoic acid that precipitated
  13. customwas collected
  14. washwashed with water
  15. customdried

출처 및 근거

ORD 기록
ord-fba4eddb5fb34a0d890c1437a6a72546
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04034007

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