Methanol → 2,4-Dimethyl-3-hydroxymethyl-5-methoxythiophene

12.0 G. (0.151 mol) of cupric oxide and 12.5 g. (0.0466 mol) of 2,4-dimethyl-3-hydroxymethyl-5-iodothiophene were added to a solution of 12.5 g. (0.543 mol) of sodium in 100 ml. of dry methanol. The reaction mixture was heated to 80°-82° C. (internal temperature) for 20 hrs. with vigorous stirring, then cooled. The cold solution was diluted with 150 ml. of methanol, filtered, poured into ice water and extracted with ether/hexane (ratio 4:1). The organic layers were washed with 5% sodium carbonate solution, dried and evaporated. The residue which resulted was recrystallized from hexane to yield 2,4-dimethyl-3-hydroxymethyl-5-methoxythiophene, m.p. 55°-60° C. This product contained about 10% of 2,4-dimethyl-3-hydroxymethylthiophene which is formed in this reaction by reduction of the iodide. Fraction recrystallization of a sample from hexane yielded pure 2,4-dimethyl-3-hydroxymethyl-5-methylthiophene, m.p. 64°-65° C.

1. temperatureThe reaction mixture was heated to 80°-82° C. (internal temperature) for 20 hrs
2. temperaturewith vigorous stirring, then cooled
3. additionThe cold solution was diluted with 150 ml
4. filtrationof methanol, filtered
5. additionpoured into ice water
6. extractionextracted with ether/hexane (ratio 4:1)
7. washThe organic layers were washed with 5% sodium carbonate solution
8. customdried
9. customevaporated
10. customThe residue which resulted
11. customwas recrystallized from hexane

ORD record

ord-52a4777bfd7e4e0787e492845b5411d6

Source dataset

uspto-grants-1977_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04061656