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Sulfuric Acid → 6-Isopropyl-2-methyl-3-cyclohexene-1-carboxylic acid

HRID 1905352
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HRID 1905352 반응식
[CH3:1][CH:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([OH:7])=[O:6].[CH2:9]=[CH:10][CH:11]=[CH:12][CH3:13].CC(C)C=CC(O)=O.S(=O)(=O)(O)O>CCOCC>[CH:2]([CH:3]1[CH:4]([C:5]([OH:7])=[O:6])[CH:12]([CH3:13])[CH:11]=[CH:10][CH2:9]1)([CH3:8])[CH3:1]
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참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 15301Penta-1,3-diene2회HCID 1121034-Methyl-pent-2-enoic acid2회HCID 6420393-Isopropyl acrylic acid

생성물 1

HCID 200354126-Isopropyl-2-methyl-3-cyclohexene-1-carboxylic acid수율 65.7%

시약·촉매·용매 1

HCID 3283
Diethyl Ether
용매

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온도
200 °C

실험 절차

A mixture of 70 g (0.61 mol) of trans-4-methyl-2-pentenoic acid and 49 g (0.72 mol) of 1,3-pentadiene was heated for 12 hours at approx. 200° C. in an autoclave. After the reaction mixture had cooled, it was checked by means of GLC for the presence of 4-methyl-2-pentenoic acid. A further 25 g (0.36 mol) of 1,3-pentadiene were added, after which the mixture was again heated for 12 hours at 200° C. This procedure was repeated until no further decrease in the content of 4-methyl-2-pentenoic acid was any longer observed. The reaction mixture obtained was dissolved in 300 ml of ether and extracted with 300 ml of 10% NaOH solution. The alkaline solution thus obtained was acidified with 40 g of concentrated sulphuric acid and then extracted three times with ether. The ether extract was washed with water, dried on MgSO4, evaporated down and distilled. 73 g of 6-isopropyl-2-methyl-3-cyclohexene-1-carboxylic acid were obtained, b.p.: 95°-100° C./70 Pa.

후처리

  1. temperatureAfter the reaction mixture had cooled
  2. temperatureafter which the mixture was again heated for 12 hours at 200° C
  3. customThe reaction mixture obtained
  4. extractionextracted with 300 ml of 10% NaOH solution
  5. customThe alkaline solution thus obtained
  6. extractionextracted three times with ether
  7. extractionThe ether extract
  8. washwas washed with water
  9. customdried on MgSO4
  10. customevaporated down
  11. distillationdistilled

출처 및 근거

ORD 기록
ord-34827857b5414388885e7bf4867918d7
출처 데이터셋
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04843061

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