Benzaldehyde → 3-Methyl-1-phenyl-1buten-1ol

To a solution of benzaldehyde (3.05 mL, 30 mmol) in THF (30 mL) was added 2-methylallylmagnesium chloride (0.8 M in THF, 45 mL, 36 mmol, 1.2 equiv) under N2 at 0° C. (internal). The mixture was warmed to room temperature and was stirred for 1.5 h. The mixture was then poured into saturated aqueous NH4Cl solution (30 mL) and was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (30 mL), then were dried (Na2SO4) and filtered. The solvent was removed by rotary evaporation and the residue was purified by Kugelrohr distillation to afford 4.33 g (89%) of 3-methyl-1-phenyl-1buten-1-ol as a colorless oil.

1. extractionwas extracted with EtOAc (2×30 mL)
2. washThe combined organic layers were washed with brine (30 mL)
3. dry with materialwere dried (Na2SO4)
4. filtrationfiltered
5. customThe solvent was removed by rotary evaporation
6. distillationthe residue was purified by Kugelrohr distillation

ORD record

ord-ff8f1e4b896a40698672aa28560c941d

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06867323B2