tert-Butanol → t-Butyl 4-hydroxy-3-nitrobenzene-acetate
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(OCC)(=O)C.[C:21](O)([CH3:24])([CH3:23])[CH3:22]>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]Participants
4
Procedure
0-t-Butyl-N,N-diisopropyl-isourea (3.65 gm, 20 mmol) was added to a solution of 4-hydroxy-3-nitrobenzene-acetic acid (3.61 gm, 18.3 mmol) in t-butanol (18 mL) and stirred for 24 hours. Ethyl acetate (100 mL) was added and the solution washed successively with water 3×25 mL), 1N sodium bicarbonate solution 3×25 mL), and saturated salt solution (25 mL). The product was isolated as a yellow oil (1.02 gm, 22% yield) and used without further purification: 1H-NMR δ (CDCl3) 1.44 (9H, s), 3.52 (2H, s), 7.08 (2H, d, J=8 Hz), 7.51 (1H, dd, J=8, 3 Hz), 8.00 (1H, d, J=3 Hz).
Workup
- washthe solution washed successively with water 3×25 mL), 1N sodium bicarbonate solution 3×25 mL), and saturated salt solution (25 mL)
Sources & evidence
- ORD record
- ord-2dd3cb1c17504ac3b2f8ed1baf6e8bc0
- Source dataset
- uspto-grants-1993_07
- Patent number
- US05229510
Reaction notes
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