反応 #6531

反応方程式

Sodium hydride

phenol

Bromoacetaldehyde diethyl acetal

→

2-phenoxyacetaldehyde diethyl acetal

溶媒

DMPU

反応条件

後処理

1. 1
   温度to cool
2. 2
   その他The mixture was partitioned between ethyl acetate (100 ml) and water (100 ml)
3. 3
   その他the organic phase was separated
4. 4
   洗浄washed sequentially with aqueous 2M sodium hydroxide solution (2×50 ml) and water (50 ml)
5. 5
   抽出re-extracted with ethyl acetate (100 ml)
6. 6
   乾燥The combined organic extracts were dried (MgSO4)
7. 7
   濃縮concentrated
8. 8
   その他The resultant oil was purified by flash column chromatography
9. 9
   洗浄eluting with ethyl acetate/hexane (1:10 v/v)

実験手順

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).

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