4-Ethoxyphenol → HCID 23716089, compound
Reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2].[OH-].[K+:12]>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([O-:10])=[CH:6][CH:5]=1)[CH3:2].[K+:12]Participants
Procedure
In a 50-ml flask at ambient temperature 4-ethoxy-phenol (Aldrich) (1492 mg, 10.8 mmoles) was stirred with 2.0 M aqueous KOH (5.50 ml) to form potassium 4-ethoxyphenolate. Methyl 4-chloro-3,5-dinitrobenzoate (Ullmann, 1909, Annalen der Chemie 366:92-93; commercial source: Spectrum Chemical Company, Gardena, Calif.; 2606 mg, 10.0 mmoles) was added, the mixture heated to reflux for 1 hour and chilled in an ice-bath, whereupon a rubbery mass of product deposited. Cold aqueous 1.0 M KOH (20 ml) was added, and 35 upon continued chilling the product solidified. The yellow-orange solid was broken-up, collected on a suction filter, rinsed with water and dried. The material (3.08 g) was crystallized from hot 95% ethanol (50 ml) to give 2.56 g (70.6% yield) of methyl 3,5-dinitro-4-(4′-ethoxyphenoxy)benzoate. Melting point: 101-103° C.
Sources & evidence
- ORD record
- ord-76c460e71e2f4b6580260eff7906577f
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326402B1
Reaction notes
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