Hydrochloric Acid → HCID 10241702, compound
Reaction equation
[C:1]([C:5]1[CH:16]=[C:15]([CH3:17])[C:8]([CH2:9][NH:10]C(=O)CCl)=[C:7]([OH:18])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C(O)C>[NH2:10][CH2:9][C:8]1[C:15]([CH3:17])=[CH:16][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:6][C:7]=1[OH:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 0.2 g of N-(4-tert-butyl-2-hydroxy-6-methylbenzyl)-2-chloroacetamide from Step A in 10 mL of 95% ethanol was added 1 mL HCl. The resulting mixture was refluxed for 4 h then aged overnight at 50° C. The reaction mixture was concentrated to remove the ethanol and then partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was dried (Na2SO4), filtered and evaporated to afford the title compound.
Workup
- temperatureThe resulting mixture was refluxed for 4 h
- customaged overnight
- customat 50° C
- concentrationThe reaction mixture was concentrated
- customto remove the ethanol
- custompartitioned between EtOAc and saturated aqueous NaHCO3
- dry with materialThe organic layer was dried (Na2SO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-267523c7cd284e4b8e8b955147071744
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589127B2
Reaction notes
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