4-Hydroxybenzaldehyde → HCID 54357442, compound

To a 500 ml egg-plant type flask, 4-hydroxybenzaldehyde (12.2 g, 100 mmol), a 28% solution of sodium methylate in methanol (18.5 ml, 130 mmol of sodium methylate), methanol (60 ml) and 6-bromo-1-hexene (20.0 ml, 150 mmol) were charged and heated under reflux for 18 hours. The reaction mixture was concentrated to about a half volume by evaporation of volatile components. Then, toluene (200 ml) and water (100 ml) were added to the concentrated mixture and shaken, followed by removal of an aqueous phase. An organic phase was washed with water (150 ml×3) and dried over anhydrous magnesium sulfate (10 g). After removing solids by filtration, volatile components were evaporated off from a filtrate to obtain 4-(1-hexenyloxy)benzaldehyde (18.9 g).

1. temperatureheated
2. temperatureunder reflux for 18 hours
3. concentrationThe reaction mixture was concentrated to about a half volume by evaporation of volatile components
4. additionThen, toluene (200 ml) and water (100 ml) were added to the concentrated mixture
5. customfollowed by removal of an aqueous phase
6. washAn organic phase was washed with water (150 ml×3)
7. dry with materialdried over anhydrous magnesium sulfate (10 g)
8. customAfter removing solids
9. filtrationby filtration, volatile components
10. customwere evaporated off from a filtrate

ORD record

ord-f5f13a3a9ec44b5283bae26b6583c35d

Source dataset

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05262502