2',4'-Dihydroxyacetophenone → 4'-Benzyloxy-2'-hydroxyacetophenone

HRID 859640

反応式

HRID 859640 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=1[C:23](=[O:25])[CH3:24]>CN(C=O)C>[CH2:7]([O:22][C:20]1[CH:19]=[CH:18][C:17]([C:23](=[O:25])[CH3:24])=[C:16]([OH:15])[CH:21]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 69902',4'-DihydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

生成物 1

HCID 3092574'-Benzyloxy-2'-hydroxyacetophenone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Potassium carbonate (54 g, 0.39 mol) followed by benzyl bromide (13.9 mL, 0.12 mol) were added to a solution of 2′,4′-dihydroxyacetophenone (20 g, 0.13 mol) in DMF (180 mL). The mixture was stirred for 5 hours and then partitioned between H2O and EtOAc. The organic layer was washed with satd NaHCO3, 1N HCl, brine, dried over Na2SO4 and concentrated to a clear oil (23.7 g, 81%). 1H NMR (400 MHz, CDCl3): δ 2.56 (s, 3 H), 5.02 (s, 2 H), 6.51 (m, 2 H), 7.33–7.43 (m, 5 H), 7.64 (d, J=8.3 Hz, 1 H), 12.73 (s, 1 H).

後処理

  1. custompartitioned between H2O and EtOAc
  2. washThe organic layer was washed with satd NaHCO3, 1N HCl, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a clear oil (23.7 g, 81%)

出典と根拠

ORDレコード
ord-55fd8ef27e7542a1973b801749637c78
出典データセット
uspto-grants-2006_12
特許番号
US07151105B2

関連ノート

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