Benzyl Bromide → 4-Pentenoic acid, phenylmethyl ester

Temperature

40 °C

To 10.53 g (105 mmol) of pent-4-enoic acid in 150 ml ethanol was added 17.1 g (52.5 mmol) of Cs2CO3 and the reaction mixture was stirred at 40° C. for 2 h. The solvent was removed in vacuo, the residue coevaporated three times with toluene and then dissolved in 150 ml of DMF. 17.96 g (105 mmol) of benzyl bromide were added and the reaction mixture stirred at room temperature for 48 h. The reaction mixture was filtered, diluted with water and extracted three times with heptane. The combined organic phases were dried over MgSO4, filtered and the solvent was removed in vacuo. Yield: 19.92 g.

1. customThe solvent was removed in vacuo
2. dissolutiondissolved in 150 ml of DMF
3. stirringthe reaction mixture stirred at room temperature for 48 h
4. filtrationThe reaction mixture was filtered
5. additiondiluted with water
6. extractionextracted three times with heptane
7. dry with materialThe combined organic phases were dried over MgSO4
8. filtrationfiltered
9. customthe solvent was removed in vacuo

ORD record

ord-5d98ee399100416ea500cf231522e00e

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06762190B2