Benzyl Alcohol → 3-(Benzyloxy)propanoic acid

Temperature

50 °C

To a stirred solution of ethylacrylate (0.5 mol, 50.0 g) in benzylalcohol (2 mol, 216 g), KtBu (5 mmol, 0.61 g) was added at room temperature. After standing overnight, NaOH (0.55 mol, 22 g) in water (100 ml) was added. The solution was stirred for 2 hrs. at 50° C. and cooled to room temperature. Water (300 ml) was added and the mixture extracted with CH2Cl2 (1×500 ml, 4×150 ml). The aqueous layer was evaporated and the residue washed with diethylether (4×100 ml). The white solid was dissolved in water (300 ml) and acidified with 33% HCl up to a pH of 2. On cooling (0° C.), the acid solidified. It was filtrated, rinsed with cold water, and dissolved in diethylether. After drying over MgSO4, the ether was evaporated. The acid was recrystallized from pentane/toluene and dried in a stream of nitrogen, resulting in 64.3 g (71%) of product.

1. extractionthe mixture extracted with CH2Cl2 (1×500 ml, 4×150 ml)
2. customThe aqueous layer was evaporated
3. washthe residue washed with diethylether (4×100 ml)
4. dissolutionThe white solid was dissolved in water (300 ml)
5. temperatureOn cooling (0° C.)
6. filtrationIt was filtrated
7. washrinsed with cold water
8. dissolutiondissolved in diethylether
9. dry with materialAfter drying over MgSO4
10. customthe ether was evaporated
11. customThe acid was recrystallized from pentane/toluene
12. customdried in a stream of nitrogen

ORD record

ord-a62fd39d0632453ab959cac09b80c29f

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05378797