反应详情

4-Chloro-3-methoxyphenol methoxymethyl ether (3.1 g, 0.0153 M) in dry ether (3.5 ml) was added dropwise to a solution of phenyllithium (from 0.21 g lithium and 2.4 g bromobanzene) in dry ether (12 ml) under nitrogen and the mixture stirred at room temperature (3 days). A solution of dry dimethylformamide (1.12 g, 0.0153 M) in dry ether (1 ml) was then added dropwise over 15 mins and the mixture stirred at room temperature (1 hr). The reaction mixture was poured into 2 N sulphuric acid (100 ml) and extracted with ethyl acetate. The combined extracts were dried (sodium sulphate) and evaporated. The residue was dissolved in methanol (25 ml), 3 N hydrochloric acid (10 ml) added and the resultant solution stirred at 65° C. for 30 mins. The solvent was removed in vacuo and the residue diluted with water (50 ml) and extracted with ether. The combined extracts were dried (sodium sulphate) and evaporated. The residue was chromatographed on silica (MFC) eluting with chloroform. The fractions were combined and evaporated to give 3-chloro-6-hydroxy-2-methoxybenzaldehyde as an oil which crystallised on standing. (Found: m/e 186.0084. C8H7ClO3 requires M185.0082).

1. stirringthe mixture stirred at room temperature (1 hr)
2. extractionextracted with ethyl acetate
3. dry with materialThe combined extracts were dried (sodium sulphate)
4. customevaporated
5. dissolutionThe residue was dissolved in methanol (25 ml)
6. addition3 N hydrochloric acid (10 ml) added
7. stirringthe resultant solution stirred at 65° C. for 30 mins
8. customThe solvent was removed in vacuo
9. additionthe residue diluted with water (50 ml)
10. extractionextracted with ether
11. dry with materialThe combined extracts were dried (sodium sulphate)
12. customevaporated
13. customThe residue was chromatographed on silica (MFC)
14. washeluting with chloroform
15. customevaporated