Sodium Hydroxide → 5-Benzyloxy-2-isopropoxybenzeneamine

HRID 1420857Notes

Reaction equation

HRID 1420857 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH:19]([CH3:21])[CH3:20])=[C:13]([N+:15]([O-])=O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)(=O)C.[Cl-].[Cl-].[Cl-].[Ti+3]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH:19]([CH3:21])[CH3:20])=[C:13]([NH2:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 187826055-Benzyloxy-2-isopropoxynitrobenzene

Product 1

HCID 187826085-Benzyloxy-2-isopropoxybenzeneamineYield 71%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Titanium trichloride (10% solution in 20-30% hydrochloric acid, 50 mL) was added to a solution of 5-benzyloxy-2-isopropoxynitrobenzene (Description 108, 2.78 g, 9.7 mmol) in acetic acid (50 mL) and the mixture was stirred at room temperature for 18 h. The mixture was poured into ice-cooled aqueous sodium hydroxide (4M, 400 mL) and the mixture was extracted with dichloromethane (8×100 mL). The combined organic fractions were washed with saturated aqueous sodium hydrogen carbonate (2×200 mL), dried MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a dark oil (1.74 g, 71%). 1H NMR (360 MHz, CDCl3) δ 7.42-7.25 (5H, m), 6.71 (1H, d, J 8.7 Hz), 6.41 (1H, d, J 2.9 Hz), 6.30 (1H, dd, J 8.7, 2.9 Hz), 4.97 (2H, s), 4.38 (1H, hept, J 6.0 Hz), 3.6 (2H, br s), and 1.32 (6H, d, d 6.0 Hz).

Workup

  1. additionThe mixture was poured into ice-
  2. extractionthe mixture was extracted with dichloromethane (8×100 mL)
  3. washThe combined organic fractions were washed with saturated aqueous sodium hydrogen carbonate (2×200 mL), dried MgSO4) and the solvent
  4. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-1e56e56e42fb4d4c923fb6611100a499
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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