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

HRID 1196263
ノート
印刷プレビュー

反応式

HRID 1196263 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 887Methanol溶媒
HCID 962Water溶媒
HCID 6386tert-Butanol溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b44ce0bea8534cb48d4fb4da9a58c4fc
出典データセット
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05112988

反応ノート

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