Hydrochloric Acid → HCID 11443388, compound

HRID 1007065Notes

Reaction equation

HRID 1007065 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([OH:19])=[CH:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](N)([CH3:23])([CH3:22])[CH3:21].Cl>[Cu](Cl)Cl.CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:17]([CH:18]=1)=[C:16]([C:21]1[C:15]([OH:19])=[CH:14][CH:13]=[C:23]3[C:20]=1[CH:22]=[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:10]=[CH:11]3)[C:15]([OH:19])=[CH:14][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 27638187-(Benzyloxy)naphthalen-2-ol

Product 1

HCID 11443388HCID 11443388, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 887MethanolSolvent3×

Procedure

To a mixture of 55.8 g (0.223 mol) of 7-benzyloxy-naphthalene-2-ol, 60.0 g (0.446 mol) of copper chloride (II), and 1.5 L of methanol was added a methanol (500 mL) solution of 130.5 g (1.78 mol) of t-butylamine, followed by 20 hours of stirring at room temperature. The reaction liquid was cooled on an ice bath and after addition of 500 mL of 6N hydrochloric acid, methanol was removed by evaporation under reduced pressure. The residue was dissolved in ethyl acetate (1.5 L) and the resulting solution was washed with saturated brine. The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel column chromatography to obtain 47.3 g of the title compound. Yield 85%.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled on an ice bath
  3. customwas removed by evaporation under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (1.5 L)
  5. washthe resulting solution was washed with saturated brine
  6. customThe solvent was removed by evaporation under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e93ed369700b462ea6da37dc394ff3c9
Source dataset
uspto-grants-2004_09
Patent number
US06794328B2

Reaction notes

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