Sulfuric Acid → 1-tert-Butyl-4-[1-(4-ethoxyphenyl)-2-nitropropyl]benzene
Reaction equation
S(=O)(=O)(O)O.[N+:6]([CH:9]([CH3:22])[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=1)O)([O-:8])=[O:7].[C:23]1([O:29][CH2:30][CH3:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[K+].[Br-]>>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([CH:10]([C:26]2[CH:27]=[CH:28][C:23]([O:29][CH2:30][CH3:31])=[CH:24][CH:25]=2)[CH:9]([N+:6]([O-:8])=[O:7])[CH3:22])=[CH:13][CH:14]=1)([CH3:21])([CH3:20])[CH3:19]Participants
Conditions
- Temperature
- 50 °C
Procedure
A 1.0 kg portion of 80% sulfuric acid was added dropwise to a solution of 237g of Example 2 in 732g of phenetole and the mixture was heated to 50° C for 2 hr. The acid layer was removed and the organic phase was diluted with ether. The ethereal solution was washed with water and with saturated sodium bicarbonate, dried over magnesium sulfate and evaporated. The crude residue which weighed 322g was triturated with 30/60 pet ether and recrystallized from isopropyl alcohol to afford a pure, white solid: mp 79°-82° C; ir (KBr) 3.4 (m), 6.5 (s), 6.6 (m), 8.0 (s), 9.5 (m), 12.2 (m) microns; nmr (CDCl3) 7.4 to 6.7 (8H, m), 5.3 (1H, doublet of quartets), 4.3 (1H, d), 3.97 (2H, q), 1.45 (3H, d), 1.29 (3H, t), 1.22 (9H, s) ppm; ms (molecular ion) 341.
Workup
- customThe acid layer was removed
- additionthe organic phase was diluted with ether
- washThe ethereal solution was washed with water and with saturated sodium bicarbonate
- dry with materialdried over magnesium sulfate
- customevaporated
- customwas triturated with 30/60 pet ether
- customrecrystallized from isopropyl alcohol
- customto afford a pure, white solid
Sources & evidence
- ORD record
- ord-52ff10a7af5e4845919389357b9e26dd
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04004023
Reaction notes
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