Réaction #6531

Équation de réaction

Sodium hydride

phenol

Bromoacetaldehyde diethyl acetal

→

2-phenoxyacetaldehyde diethyl acetal

Solvants

DMPU

Conditions de réaction

Traitement

1. 1
   Températureto cool
2. 2
   AutreThe mixture was partitioned between ethyl acetate (100 ml) and water (100 ml)
3. 3
   Autrethe organic phase was separated
4. 4
   Lavagewashed sequentially with aqueous 2M sodium hydroxide solution (2×50 ml) and water (50 ml)
5. 5
   Extractionre-extracted with ethyl acetate (100 ml)
6. 6
   SéchageThe combined organic extracts were dried (MgSO4)
7. 7
   Concentrationconcentrated
8. 8
   AutreThe resultant oil was purified by flash column chromatography
9. 9
   Lavageeluting with ethyl acetate/hexane (1:10 v/v)

Mode opératoire

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).

Source