Benzyl Salicylate → Benzyl 2-[2,6-Bis(isopropyl)phenoxycarbonyloxy]-benzoate

HRID 2103788

反応式

HRID 2103788 の反応式
[C:1]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(N(CC)CC)C.[CH:25]([C:28]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[C:29]=1[O:30][C:31](Cl)=[O:32])([CH3:27])[CH3:26]>ClCCl.CN(C1C=CN=CC=1)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH:25]([C:28]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[C:29]=1[O:30][C:31]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:32])([CH3:27])[CH3:26]

参加物

7

反応物 3

HCID 8363Benzyl SalicylateHCID 8471TriethylamineHCID 2716192,6-Di(propan-2-yl)phenyl carbonochloridate

生成物 1

HCID 21110017Benzyl 2-[2,6-Bis(isopropyl)phenoxycarbonyloxy]-benzoate収率 57%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 311Citric Acid溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a cooled (0° C.) solution of benzyl salicylate (0.77 g, 3.3 mmol) in dichloromethane (6 mL) was added triethylamine (0.52 mL, 3.7 mmol) and a catalytic amount of DMAP. To this mixture a suspension of compound (104) (0.9 g, 3.7 mmol, crude product from last step) in dichloromethane (4 mL) was further added. The reaction was allowed to warm to room temperature slowly and stirred for 14 h. The reaction mixture was then diluted with 10% aqueous citric acid solution (10 mL) and extracted with ethyl ether (2×40 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified by radial chromatography on silica gel (eluting with ethyl acetate/hexane) to afford 0.8 g (57% yield over two steps) of the title compound (105).

後処理

  1. additionwas further added
  2. extractionextracted with ethyl ether (2×40 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by radial chromatography on silica gel (eluting with ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-274f4251ac5f470e866c915c104f7fc3
出典データセット
uspto-grants-2009_08
特許番号
US07576127B2

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