Sodium hydride → HCID 1480959, compound

4-Methylquinol-2-one (24.0 g.) was added in portions to a stirred suspension of sodium hydride [6.5 g.; weighed as a 60% w/w dispersion in oil, but subsequently washed by decantation with petroleum ether (b.p. 40°-60° C.)] in dimethylformamide (150 ml.), at 20°-25° C. After the addition was complete the mixture was stirred at 20°-25° C. for a further 1 hour. Benzyl chloride (23.0 g.) was then added and the subsequent mixture was heated at 95°-100° C. for 20 hours. The mixture, which contained some solid, was then added to water (1 liter) and the resultant mixture was stirred for 1 hour. The solid which formed was separated by filtration, washed with water, and then was resuspended in a mixture of water (300 ml.) and 2 N hydrochloric acid (50 ml.). This mixture was stirred for 15 minutes and then the solid separated by filtration to give 1-benzyl-4-methylquinol-2-one, as a white crystalline solid, 20.0 g., m.p. 109°-111° C. after recrystallisation from cyclohexane.

1. washsubsequently washed by decantation with petroleum ether (b.p. 40°-60° C.)] in dimethylformamide (150 ml.)
2. customat 20°-25° C
3. additionAfter the addition
4. additionBenzyl chloride (23.0 g.) was then added
5. temperaturethe subsequent mixture was heated at 95°-100° C. for 20 hours
6. additionwas then added to water (1 liter)
7. stirringthe resultant mixture was stirred for 1 hour
8. customThe solid which formed
9. customwas separated by filtration
10. washwashed with water
11. additionwas resuspended in a mixture of water (300 ml.) and 2 N hydrochloric acid (50 ml.)
12. stirringThis mixture was stirred for 15 minutes
13. customthe solid separated by filtration

ORD record

ord-fa2635cb492c4870a0d16fbd7599c84c

Source dataset

uspto-grants-1980_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04187310