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

HRID 2103788

Reaction equation

HRID 2103788 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 311Citric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-274f4251ac5f470e866c915c104f7fc3
Source dataset
uspto-grants-2009_08
Patent number
US07576127B2

Linked notes

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