Water → Ethyl (p-tolyloxy)acetate

A stirred mixture of p-cresol (14.6 g, 0.135 mole) and anhydrous potassium carbonate (37.2 g, 0.27 mole) in dry acetone (200 ml) was heated under reflux for 30 minutes. The mixture was then cooled to room temperature and ethyl bromoacetate (16.6 ml, 0.15 mole) added. The mixture was heated upto reflux again and maintained at this temperature for 41/2 hours, then allowed to cool before pouring into water (1000 ml). The aqueous mixture was extracted with ether (2×250 ml) and the organic solution washed with dilute hydrochloric acid (1×200 ml) and water (1×200 ml), then dried (MgSO4) and evaporated to dryness to give a quantitative yield of the title compound as a yellow oil.

1. temperaturewas heated
2. temperatureunder reflux for 30 minutes
3. temperatureThe mixture was heated
4. temperatureupto reflux again
5. temperaturemaintained at this temperature for 41/2 hours
6. temperatureto cool
7. extractionThe aqueous mixture was extracted with ether (2×250 ml)
8. washthe organic solution washed with dilute hydrochloric acid (1×200 ml) and water (1×200 ml)
9. dry with materialdried (MgSO4)
10. customevaporated to dryness

ORD record

ord-5fdd0576a61d4e31adbd02c7e8bc3dd1

Source dataset

uspto-grants-1985_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04548948