반응 #6531

반응 방정식

Sodium hydride

phenol

Bromoacetaldehyde diethyl acetal

→

2-phenoxyacetaldehyde diethyl acetal

용매

DMPU

반응 조건

후처리

1. 1
   온도to cool
2. 2
   기타The mixture was partitioned between ethyl acetate (100 ml) and water (100 ml)
3. 3
   기타the organic phase was separated
4. 4
   세척washed sequentially with aqueous 2M sodium hydroxide solution (2×50 ml) and water (50 ml)
5. 5
   추출re-extracted with ethyl acetate (100 ml)
6. 6
   건조The combined organic extracts were dried (MgSO4)
7. 7
   농축concentrated
8. 8
   기타The resultant oil was purified by flash column chromatography
9. 9
   세척eluting with ethyl acetate/hexane (1:10 v/v)

실험 절차

Sodium hydride (5.83 g of a 55% dispersion in mineral oil) was added to a solution of phenol (12.56 g) in DMPU (25 ml) at 5° C. and the mixture was stirred for 30 minutes. Bromoacetaldehyde diethyl acetal (10.05 ml) was added and the mixture was heated at 110° C. for 5 hours, then allowed to cool. The mixture was partitioned between ethyl acetate (100 ml) and water (100 ml) and the organic phase was separated and washed sequentially with aqueous 2M sodium hydroxide solution (2×50 ml) and water (50 ml). The aqueous fractions were combined and re-extracted with ethyl acetate (100 ml). The combined organic extracts were dried (MgSO4) and concentrated. The resultant oil was purified by flash column chromatography, eluting with ethyl acetate/hexane (1:10 v/v) to give 2-phenoxyacetaldehyde diethyl acetal (9.43 g) as an oil; NMR: 1.25(6H,t, J=7.0 Hz), 3.6-3.85(4H,m), 4.05(2 H,d, J=6.0 Hz), 4.85 (1H,t, J=6.0 Hz) and 6.9-7.35(5H,m).

출처