Salicylic Acid → Benzyl Salicylate

HRID 1259016

反応式

HRID 1259016 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7]Br)=[CH:3][CH:2]=1.[C:9]([OH:18])(=[O:17])[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[OH:12].O>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[OH:12][C:11]1[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=1[C:9]([O:18][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[O:17]

参加物

5

反応物 3

HCID 338Salicylic AcidHCID 962WaterHCID 7498Benzyl Bromide

生成物 1

HCID 8363Benzyl Salicylate収率 76%

試薬・触媒・溶媒 1

HCID 2724141Tetrabutylammonium Fluoride溶媒

実験手順

BnBr (1.75 mL, 14.631 mmol) was added to a solution of salicylic acid (2.0 g, 14.625 mmol) in TBAF (17.5 mL, 1 M solution in THF) and the reaction mixture was stirred at r.t. overnight (16 h). The organic layer was poured into H2O (100 mL) and extracted with EtOAc (70 mL). It was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (2% EtOAc/hexanes) to furnish 2.53 g of benzyl 2-hydroxybenzoate (colourless oil, yield: 76%).

後処理

  1. extractionextracted with EtOAc (70 mL)
  2. dry with materialIt was dried over Na2SO4 (anhydrous)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on SiO2 (2% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-0f302b53436d46b8bb7f6b02c2d94567
出典データセット
uspto-grants-2013_06
特許番号
US08466197B2

関連ノート

読み込み中…