Furfural → 2-Furyl(phenyl)methanol

A solution of furfuraldehyde (288 g.) in diethyl ether (400 ml.) was added over 30 minutes to a stirred solution of phenyl magnesium bromide [prepared from bromobenzene (314 g.) and magnesium (48 g.)] in diethyl ether (1400 ml.) at -25° C. The cooling bath was removed and the mixture was allowed to attain 10° C. over 30 minutes. The mixture was recooled to 0° C. and saturated aqueous ammonium chloride solution was added at that temperature. The mixture was diluted with water (2 liters) and the organic phase was separated. The aqueous phase was filtered and extracted with diethyl ether (3 × 200 ml.) and the combined etheral solutions were dried over sodium sulphate, filtered and evaporated to dryness. The resulting pale red oil was distilled to give (±) 2-(α-hydroxybenzyl)furan (240 g.), b.p. 110°-130° C./0.05 mm.Hg.

1. customThe cooling bath was removed
2. customwas recooled to 0° C.
3. additionsaturated aqueous ammonium chloride solution was added at that temperature
4. additionThe mixture was diluted with water (2 liters)
5. customthe organic phase was separated
6. filtrationThe aqueous phase was filtered
7. extractionextracted with diethyl ether (3 × 200 ml.)
8. dry with materialthe combined etheral solutions were dried over sodium sulphate
9. filtrationfiltered
10. customevaporated to dryness
11. distillationThe resulting pale red oil was distilled

ORD record

ord-27d66727d02c47ef9478be8c1a8241f0

Source dataset

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04067723