Hydrochloric Acid → [3-(2-Hydroxy-1-methylethyl)-4-nitrophenyl]phenylmethanone

HRID 2357145ノート

反応式

HRID 2357145 の反応式
[OH:1][CH2:2][CH:3]([C:5]1[CH:6]=[C:7]([C:14]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)OCCC[O:15]2)[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH3:4].Cl>C(O)C.O>[C:14]([C:7]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:5]([CH:3]([CH3:4])[CH2:2][OH:1])[CH:6]=1)(=[O:15])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 59386295HCID 59386295、化合物

生成物 1

HCID 59386296[3-(2-Hydroxy-1-methylethyl)-4-nitrophenyl]phenylmethanone収率 91%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

To a solution of 2-(3-(2-hydroxy-1-methylethyl)-4-nitrophenyl)-2-phenyl-1,3-dioxane (18) (23.6 g; approx. 69 mmol) in ethanol (350 mL) was added water (70 mL) under vigorous stirring. Concentrated hydrochloric acid (about 12 N aqueous solution, 35 mL) was then added drop wise. The reaction mixture was stirred at ambient temperature for 4 hours, diluted with water and extracted with ethyl acetate. The organic phase was successively washed with an aqueous, saturated solution of NaHCO3 and with water. The organic phase was then concentrated in vacuo and seeded with crystals of the product 4f to provide a yellow solid. Finally, the powdered solid was washed with hexane and air dried to yield 17.83 g (62.5 mmol, 91%) of a yellow powder. 1H NMR (250 MHz, DMSO-d6) δ 7.91-7.52 (m, 8H, arom.), 4.75 (br. s., 1H, OH), 3.53 (d, 2H, α-CH2), 3.23 (sextet, 1H, β-CH), 1.24 (d, 3H, γ-CH3).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was successively washed with an aqueous, saturated solution of NaHCO3
  3. concentrationThe organic phase was then concentrated in vacuo
  4. customto provide a yellow solid
  5. washFinally, the powdered solid was washed with hexane and air
  6. customdried

出典と根拠

ORDレコード
ord-0adb48d2fe844b3ebedf6f2d406fc6f8
出典データセット
uspto-grants-2010_07
特許番号
US07759513B2

反応ノート

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