Hydrochloric Acid → HCID 10241702, compound

HRID 733306Notes

Reaction equation

HRID 733306 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

HCID 313Hydrochloric AcidHCID 68715625HCID 68715625, compound

Product 1

HCID 10241702HCID 10241702, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. temperatureThe resulting mixture was refluxed for 4 h
  2. customaged overnight
  3. customat 50° C
  4. concentrationThe reaction mixture was concentrated
  5. customto remove the ethanol
  6. custompartitioned between EtOAc and saturated aqueous NaHCO3
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-267523c7cd284e4b8e8b955147071744
Source dataset
uspto-grants-2009_09
Patent number
US07589127B2

Reaction notes

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