Benzyl 3,4,5-tris(benzyloxy)benzoate → 3,4,5-Tris(benzyloxy)benzoic Acid
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:22]=[C:23]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:24]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:12]([O:14]CC1C=CC=CC=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[OH-].[K+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:22]=[C:23]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:24]=1[O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1a (4 gm, 7.54 mmol) in ethanol (40 mL), 20% KOH solution (10 mL) was added. The reaction mixture was refluxed for 2 h. Ethanol was evaporated under a vacuo, and was neutralized by 6 N HCL. The combined mixture was extracted in EtOAc (3×20 mL), washed with brine solution (20 mL). The organic layer was dried over Na2SO4 and evaporated to dryness. The crude residue was purified by silica gel column chromatography using 30% ethyl acetate in hexane as eluent to obtain pure compound 3,4,5-tris(benzyloxy)benzoic acid (1b) as white solid (2.78 g, 84%). Rf=0.515 (50% ethyl acetate in hexane)
Workup
- temperatureThe reaction mixture was refluxed for 2 h
- customEthanol was evaporated under a vacuo
- extractionThe combined mixture was extracted in EtOAc (3×20 mL)
- washwashed with brine solution (20 mL)
- dry with materialThe organic layer was dried over Na2SO4
- customevaporated to dryness
- customThe crude residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-109517562d164d0c8b1fd67e4e33f961
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901317B2
Reaction notes
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