4-Hydroxybenzaldehyde → 4-(1,3-dithian-2-yl)phenol

Temperature

0 °C

4-Hydroxybenzaldehyde (46 g, 0.377 mol), recrystallized from benzene, and 1,3-propanedithiol (45 ml, 0.449 mol) were added to dry chloroform. The reaction mixture was stirred at 0° C. and HCl gas was bubbled through the solution for 10 minutes. After the exothermic reaction stopped the solution was refluxed for 10 hours. A white precipitate formed. This was filtered off and the chloroform solution was washed with water three times, dried (MgSo4) and evaporated under reduced pressure to yield a light yellow solid. White needles were obtained after recrystallization from chloroform, MP=151°-152° C. The white precipitate was also recrystallized from chloroform to yield white needles that melted at 151°-152° C. IR and NMR confirmed the two compounds to be identical. Total yield after recrystallization: 99%.

1. customHCl gas was bubbled through the solution for 10 minutes
2. customAfter the exothermic reaction
3. temperaturewas refluxed for 10 hours
4. customA white precipitate formed
5. filtrationThis was filtered off
6. washthe chloroform solution was washed with water three times
7. customdried (MgSo4)
8. customevaporated under reduced pressure
9. customto yield a light yellow solid
10. customWhite needles were obtained
11. customafter recrystallization from chloroform, MP=151°-152° C
12. customThe white precipitate was also recrystallized from chloroform
13. customto yield white needles that melted at 151°-152° C
14. customTotal yield
15. customafter recrystallization

ORD record

ord-a9ea42a8920347699869a283c09658dc

Source dataset

uspto-grants-1987_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04661611