Salicylic Acid → Benzyl Salicylate

HRID 1259016

반응식

HRID 1259016 반응식
[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]

참가 물질

5

반응물 3

HCID 338Salicylic AcidHCID 962WaterHCID 7498Benzyl Bromide

생성물 1

HCID 8363Benzyl Salicylate수율 76%

시약·촉매·용매 1

HCID 2724141Tetrabutylammonium Fluoride용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-0f302b53436d46b8bb7f6b02c2d94567
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466197B2

연결된 노트

불러오는 중…