Sodium Hydroxide → 1-(2,2-Diphenyl-benzo(1,3)dioxol-5-yl)-propan-1-one

HRID 1003632

反応式

HRID 1003632 の反応式
[CH3:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([OH:12])[CH:6]=1)=[O:4].Cl[C:14](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>>[C:15]1([C:14]2([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:11][C:8]3[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][CH3:1])=[CH:6][C:7]=3[O:12]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

4

反応物 3

HCID 14798Sodium HydroxideHCID 16327DichlorodiphenylmethaneHCID 962673',4'-Dihydroxypropiophenone

生成物 1

HCID 211866231-(2,2-Diphenyl-benzo(1,3)dioxol-5-yl)-propan-1-one

反応条件

温度
170 °C

実験手順

A mixture of 3,4-dihydroxypropiophenone (ICN Biomedicals, Inc., 3300 Hyland Ave., Costa Mesa, Calif., 92626, USA, 5.0 g, 30 mmol) and dichlorodiphenylmethane (10.0 mL, 52.1 mmol) was heated for 7 min at 170° C. The reaction was cooled and poured into 1 N sodium hydroxide. The mixture was extracted with ether (2×) and the combined extracts were washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated. The residue was flash chromatographed on silica gel (2×5 inches packed in hexane) with elution proceeding as follows: 2% ether/hexane (500 mL), 0.84 g of a white solid tentatively identified as 2-chloro-1-(2,2-diphenyl-benzo(1,3)dioxol-5-yl)-propan-1-one; 5% ether/hexane (250 mL), 1.9 g of an unidentified orange oil; 5% ether/hexane (250 mL), 2.18 g of recovered dichlorodiphenylmethane; 10% ether/hexane (500 mL), 4.82 g (48%) of 1-(2,2-diphenyl-benzo(1,3)dioxol-5-yl)-propan-1-one as an orange oil which solidified on standing. The product had: mp 69-70.5° C. Analysis calculated for C22H17ClO3 : C, 79.98; H, 5.49. Found: C, 80.05; H, 5.34.

後処理

  1. temperatureThe reaction was cooled
  2. extractionThe mixture was extracted with ether (2×)
  3. washthe combined extracts were washed with water and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customchromatographed on silica gel (2×5 inches packed in hexane) with elution proceeding

出典と根拠

ORDレコード
ord-f4dd91c93dae471bab73d7cad9662e9f
出典データセット
uspto-grants-2000_04
特許番号
US06046213

関連ノート

読み込み中…