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Propylene Glycol → 2-Hydroxypropyl 4-nitrobenzoate

HRID 8486
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HRID 8486 반응식
[OH:1][CH:2]([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].ClCCl>C1(C)C=CC=CC=1>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:4][CH2:3][CH:2]([OH:1])[CH3:5])=[O:21])=[CH:23][CH:24]=1)([O-:15])=[O:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1030Propylene GlycolHCID 6344DichloromethaneHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chloride

생성물 1

HCID 153548462-Hydroxypropyl 4-nitrobenzoate수율 51%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

2-Hydroxypropanol (4.57 g) was dissolved in toluene (80 ml) by stirring and triethylamine (6.68 g) was dropped thereinto at 0° C. After stirring at the same temperature for 30 minutes, a solution of p-nitrobenzoyl chloride (11.4 g) dissolved in toluene (12 ml) was slowly added thereto. The resultant mixture was heated to room temperature and stirred for 2 hours. Next, dichloromethane (50 ml) was added and the crystals thus precipitated were dissolved. The solution was washed with an dilute aqueous solution of sodium hydrogencarbonate (100 ml) and then with an aqueous solution of hydrochloric acid (0.5 mol/l). The organic layer thus obtained was concentrated and the residue was dissolved in toluene (45 ml) by heating. Then it was cooled by allowed to stand at room temperature for crystallization. The crystals thus precipitated were collected by filtration and dried under reduced pressure to give 6.90 g (51%) of the title compound as yellow crystals.

후처리

  1. customat 0° C
  2. stirringAfter stirring at the same temperature for 30 minutes
  3. additionwas slowly added
  4. stirringstirred for 2 hours
  5. customthe crystals thus precipitated
  6. dissolutionwere dissolved
  7. washThe solution was washed with an dilute aqueous solution of sodium hydrogencarbonate (100 ml)
  8. customThe organic layer thus obtained
  9. concentrationwas concentrated
  10. dissolutionthe residue was dissolved in toluene (45 ml)
  11. temperatureby heating
  12. temperatureThen it was cooled
  13. customto stand at room temperature for crystallization
  14. customThe crystals thus precipitated
  15. filtrationwere collected by filtration
  16. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-1821794b14ae472f84774307a0bd3dd8
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07087778B2

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