Hydrochloric Acid → 2-(Benzyloxy)-4-nitrophenol
Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[O:18]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.[OH-].[Na+].Cl>O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[OH:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A 200 mL round bottomed flask is charged with 2-(benzyloxy)-1-methoxy-4-nitrobenzene (10.00 g, 38.6 mmol) and DMSO (30 mL). To the stirred suspension is added NaOH (10 N, 10 mL, 100 mmol), and the mixture is heated to 100° C. for 5 h. The solution is cooled to rt, and immersed in a water ice bath, and water (30 mL) is added to the solution. The pH is adjusted to ˜1 by addition of concentrated HCl (10 mL, 121 mmol). The solution is extracted once with toluene (80 mL). The organic phase is washed successively with water (20 mL) and brine (20 mL), and evaporated to dryness yielding 9.37 g (99%) of the title compound as a yellow solid. LCMS (Standard Method): 2.70 min, 268 (M+Na)+. 1NMR (300 MHz, CDCl3) δ 7.92-7.86 (m, 2H), 7.45-7.41 (m, 5H), 7.00 (d, J=8.8 Hz, 1H), 5.20 (s, 2H).
Workup
- temperatureThe solution is cooled to rt
- customimmersed in a water ice bath
- extractionThe solution is extracted once with toluene (80 mL)
- washThe organic phase is washed successively with water (20 mL) and brine (20 mL)
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-19a1db997cf348ac9047b53e068ec9e7
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466296B2
Reaction notes
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