Hydrochloric Acid → Benzoic acid, 4-ethoxy-, ethyl ester
Reaction equation
[Na].[O:2]=O.[CH2:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([OH:18])C(Cl)(Cl)Cl)=[CH:9][CH:8]=1)[CH3:5].Cl.[CH2:20](O)[CH3:21]>O.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[CH2:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([O:18][CH2:20][CH3:21])=[O:2])=[CH:11][CH:12]=1)[CH3:5]Participants
Procedure
Cupric chloride dihydrate (0.125 g; 0.733 m. moles) and 1,10-phenanthroline hydrate (0.375 g; 1.9 m. moles) were added to a solution of sodium (1.15 g; 50 m. moles) in ethanol (75 ml). A stream of dry oxygen was passed through the mixture, 1-(4-ethoxyphenyl)-2,2,2-trichloroethanol (11.72 g; 43.6 m. moles) added and the mixture stirred at 30°-35° C. for 11/2 hours. A solution of sodium (0.575 g; 25 m. moles) in ethanol (10 ml) was then added and the reaction was allowed to continue for a further 1 hour. The reaction mixture was diluted with water (250 ml), acidified with hydrochloric acid and extracted with ether (3×50 ml). The combined ether extracts were washed once with water and twice with dilute aqueous sodium carbonate, dried (MgSO4) and evaporated. The residue was distilled to give ethyl 4-ethoxybenzoate (5.3 g; yield 66%), b.p. 148°-150° C./12 mm.
Workup
- additionadded
- waitto continue for a further 1 hour
- extractionextracted with ether (3×50 ml)
- washThe combined ether extracts were washed once with water and twice with dilute aqueous sodium carbonate
- dry with materialdried (MgSO4)
- customevaporated
- distillationThe residue was distilled
Sources & evidence
- ORD record
- ord-7c578ed1ab7b45ab9780c2547d5c1fcd
- Source dataset
- uspto-grants-1981_02
- Patent number
- US04249015
Reaction notes
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