Potassium Carbonate → HCID 86599434, compound

Methyl glycolate (10.4 g, 114 mmol), crotyl alcohol (100 ml, excess), was refluxed in the presence of K2CO3 (0.8 g) for 1 hr, during which time about 10 ml of the condensate was removed through a Dean-Stock trap. After diluting with hexane (100 ml), the solid was filtered through a short silica gel column (50 g), washed with 1:5 ethylacetate:hexane (250 ml). The combined filtrate and washings was concentrated to 100 ml, and was diluted again with hexane (100 ml), passed through silica gel column and washed. The solution was concentrated to ˜12.5 g of oil, which was vacuum distilled to give crotyl glycolate: 9.3 g (97° C./20 mmHg) as a mixture of cis:trans (1:10). NMR (500 MHz, CDCl3) δ: 1.3 (m, 3H), 4.15 (s, 2H), 4.62 (d, 2H), 5.6 (m, 1H), 5.84 (m, 1H). cis isomer: 1.71 (m, 3H), the rest peaks overlaps with trans isomer.

1. customwas removed through a Dean-Stock trap
2. additionAfter diluting with hexane (100 ml)
3. filtrationthe solid was filtered through a short silica gel column (50 g)
4. washwashed with 1:5 ethylacetate
5. concentrationThe combined filtrate and washings was concentrated to 100 ml
6. additionwas diluted again with hexane (100 ml)
7. washwashed
8. concentrationThe solution was concentrated to ˜12.5 g of oil, which
9. distillationdistilled

ORD record

ord-db9b73dacfa84f6f8103b4b29ead54f9

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504425B2