Acetic Acid → 3',5'-Bis(tert-butyl)-4'-hydroxyacetophenone

HRID 1441134ノート

反応式

HRID 1441134 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[C:16](O)(=[O:18])[CH3:17]>FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(Cl)(Cl)Cl>[C:11]([C:7]1[CH:8]=[C:9]([C:16](=[O:18])[CH3:17])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 314052,6-Di-tert-butylphenol

生成物 1

HCID 6162963',5'-Bis(tert-butyl)-4'-hydroxyacetophenone

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 9845Trifluoroacetic anhydride溶媒

実験手順

A mixture of 2,6-di-t-butylphenol (1 g) in trifluoroacetic anhydride (5 ml) is carefully treated with 0.28 ml of glacial acetic acid and the reaction mixture is stirred at 20°-25° for 1 hr. The reaction mixture is diluted with chloroform and is separated, washed with saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product (1.39 g) is chromatographed on 180 g of silica gel. The column is packed and eluted with chloroform/acetone (99/1). An initial fraction of 200 ml is collected, followed by 7 ml fractions. Based on their TLC homogeniety, fractions 20-55 are combined and concentrated. Recrystallized from hexane gives the tire compound, mp 148°-150°; IR (mineral oil) 3581, 3007, 2956, 2925, 2871, 2856, 1663, 1596, 1581, 1465, 1463, 1442, 1423, 1370, 1364, 1356, 1320, 1305, 1274, 1239, 1232, 1138, 1124, 1108 an 886 cm-1 ; NMR (CDCl3, TMS) 7.84, 5.73, 2.56, and 1.47δ; CMR (CDCl3, TMS) 197.6, 158, 4, 135.8, 129.1, 126.1, 34.4, 30.2 and 26.3δ; MS (m/z) M+ (found)=248; other ions at m/z 233, 217, 205, 189, 178, 115, 57 and 43.

後処理

  1. customis separated
  2. washwashed with saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product (1.39 g) is chromatographed on 180 g of silica gel
  6. washeluted with chloroform/acetone (99/1)
  7. customAn initial fraction of 200 ml is collected
  8. concentrationconcentrated
  9. customRecrystallized from hexane
  10. customgives the tire compound, mp 148°-150°

出典と根拠

ORDレコード
ord-94d0f2f2ae774db6b15d01047487178b
出典データセット
uspto-grants-1996_03
特許番号
US05502187

反応ノート

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