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Hydrochloric Acid → 4,4-Diphenyl-2-formyl-3-(nitromethyl)cyclohexanone

HRID 1196263
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인쇄 미리보기

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HRID 1196263 반응식
[C:1]1([C:7]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][C:10](=[O:13])[C:9]([CH:14]=[O:15])=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:22]([CH3:25])([O-:24])=[O:23].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.Cl>O1CCCC1.C(O)(C)(C)C.CO.C(OCC)(=O)C.O>[C:1]1([C:7]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][C:10](=[O:13])[CH:9]([CH:14]=[O:15])[CH:8]2[CH2:25][N+:22]([O-:24])=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 66854Benzyltrimethylammonium hydroxideHCID 537947534,4-Diphenyl-2-formyl-2-cyclohexen-1-one

생성물 1

HCID 540830574,4-Diphenyl-2-formyl-3-(nitromethyl)cyclohexanone

시약·촉매·용매 5

HCID 887Methanol
용매
HCID 962Water용매
HCID 6386tert-Butanol용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

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온도
20 °C

실험 절차

A solution of 4,4-diphenyl-2-formyl-2-cyclohexen-1-one (29 g) and nitromethane (5.7 cc) in a mixture of tetrahydrofuran (250 cc) and tert-butanol (500 cc) is treated with a 35% strength solution (6.93 cc) of benzyltrimethylammonium hydroxide in methanol and stirred at 20° C. for 18 hours. The reaction mixture is diluted with ethyl acetate (500 cc) and water (2000 cc) and acidified to pH 2 with hydrochloric acid. The aqueous phase is extracted with ethyl acetate (200 cc) and the combined organic phases are washed with water (500 cc) and saturated sodium chloride solution (250 cc), then dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The crystallized residue is stirred in a mixture (100 cc) of cyclohexane and ethyl acetate (80:20 by volume) and the crystals are drained and washed with the same mixture (20 cc) and with isopropyl ether (2×50 cc). 4,4-Diphenyl-2-formyl-3-(nitromethyl)cyclohexanone (24.7 g) is obtained in the form of cream-colored crystals, m.p. 188° C.

후처리

  1. extractionThe aqueous phase is extracted with ethyl acetate (200 cc)
  2. washthe combined organic phases are washed with water (500 cc) and saturated sodium chloride solution (250 cc)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. stirringThe crystallized residue is stirred in a mixture (100 cc) of cyclohexane and ethyl acetate (80:20 by volume)
  6. washwashed with the same mixture (20 cc) and with isopropyl ether (2×50 cc)

출처 및 근거

ORD 기록
ord-b44ce0bea8534cb48d4fb4da9a58c4fc
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05112988

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