Hydrochloric Acid → HCID 11443388, compound

HRID 481794Notes

Reaction equation

HRID 481794 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=2)[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>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16]([CH:15]=[CH:14][C:13]([OH:19])=[C:12]2[C:14]2[C:23]3[C:20](=[CH:22][CH:18]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[CH:21]=[CH:12][C:13]=2[OH:19])=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 11443388HCID 11443388, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 23.6 g (0.094 mol) of 2-benzyloxy-7-hydroxynaphthalene and 25.6 g (0.19 mol) of cupric chloride was added 600 ml of methanol, and 56.32 g (0.77 mol) of t-butylamine and 200 ml of methanol were added thereto dropwise over a period of 1.5 hours, followed by stirring for 20 hours. The reaction mixture was cooled with an ice bath, and 200 ml of a 6N hydrochloric acid aqueous solution was added thereto dropwise. The reaction mixture was concentrated with an evaporator. Ethyl acetate was added to the residue, followed by liquid-liquid separation. The organic layer was washed with a saturated sodium chloride aqueous solution, and the solvent was removed by evaporation. The residue was recrystallized from toluene-cyclohexane to yield 20 g (85%) of the title compound.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was cooled with an ice bath
  3. concentrationThe reaction mixture was concentrated with an evaporator
  4. additionEthyl acetate was added to the residue
  5. customfollowed by liquid-liquid separation
  6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  7. customthe solvent was removed by evaporation
  8. customThe residue was recrystallized from toluene-cyclohexane

Sources & evidence

ORD record
ord-e16b001de3fa40f7a4b5d49ac38aa388
Source dataset
uspto-grants-1998_08
Patent number
US05789609

Reaction notes

Loading…