Formic Acid → Bicyclo(2.2.1)hept-5-ene-2-methanol

Norbornen-5-ol (25 g) was dissolved at 55° C. in 100 mL of formic acid (96%). Unless otherwise specified, all of the reagents specified in the examples herein are obtained from the Aldrich Chemical Co. After 2 hours gas chromatography (GC) indicated that all norbornen-5-ol was consumed. The reaction mixture was cooled down and 100 mL of ether was added. Then, the reaction mixture was extracted with 10×100 mL of water. The organic layer was separated, dried and ether was removed. The product was distilled at 75° C. (20 mm Hg). Yield: 17 g, 54% (95% pure by GC, no OH peak by IR). The same procedure afforded formyl ester of norbornen-5-methanol with 37% yield (b. p. 85° C., 20 mm Hg, 96% pure by GC).

1. customherein are obtained from the Aldrich Chemical Co
2. customwas consumed
3. temperatureThe reaction mixture was cooled down
4. addition100 mL of ether was added
5. extractionThen, the reaction mixture was extracted with 10×100 mL of water
6. customThe organic layer was separated
7. customdried
8. customether was removed
9. distillationThe product was distilled at 75° C. (20 mm Hg)

ORD record

ord-3801ed196f0840118fda37637e26fbf0

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06048664