Hydrochloric Acid → 5-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzoic acid
Reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([Cl:22])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[CH:10]=[O:11].CC(=CC)C.Cl([O-])=[O:29].[Na+].Cl>C1COCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)(C)(C)C>[Cl:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([Cl:22])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[C:10]([OH:29])=[O:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-benzaldehyde (3.0 g, 8.8 mmol) in a mixture of THF (50 ml), tert-butyl alcohol (50 ml) and 2-methyl-2-butene (11 ml, 132 mmol) was added dropwise a solution of sodium chlorite (7.1 g, 79 mmol) in potassium phosphate buffer (100 ml of a 0.6 M solution, 60 mmol). The resulting mixture was stirred vigorously for 16 h at RT then acidified with 1 M HCl (200 ml). The resulting mixture was extracted with EtOAC (3×150 ml). The combined EtOAc extracts were washed with 1 M HCl (2×250 ml), water (250 ml), 10% NaHSO3, and brine (250 ml). The extracts were dried (Na2SO4), filtered, and concentrated to give the title compound of Step B (3.1 g) as a yellow solid. The title product of Step B was used in the next step without further purification. MS (ES−) Calc.: 357.0, Found: 356.0 (M−1).
Workup
- extractionThe resulting mixture was extracted with EtOAC (3×150 ml)
- washThe combined EtOAc extracts were washed with 1 M HCl (2×250 ml), water (250 ml), 10% NaHSO3, and brine (250 ml)
- dry with materialThe extracts were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c88c493b7f614d808179a44c1c0b88ab
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06664291B2
Reaction notes
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