Benzyl Bromide → 4-Pentenoic acid, phenylmethyl ester

HRID 707669Notes

Reaction equation

HRID 707669 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([OH:15])(=[O:14])[CH2:10][CH2:11][CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:15][C:9](=[O:14])[CH2:10][CH2:11][CH:12]=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 611384-Pentenoic acid

Product 1

HCID 100520354-Pentenoic acid, phenylmethyl ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

Benzyl bromide (7.19 g, 42.04 mmol) was added to a solution of 4-pentenoic acid (6) (5.05 g, 50.45 mmol, 1.2 eq.) in acetone (75 ml) at RT under N2. Anhydrous potassium carbonate (29.05 g, 210.19 mmol, 5.0 eq.) and tetrabutylammonium iodide (0.776 g, 2.102 mmol, 0.05 eq.) were added and the resulting suspension was stirred over 2 days. LCMS analysis showed mainly product.

Sources & evidence

ORD record
ord-439d5aef3c3846a581ca6f50f0f9aee2
Source dataset
uspto-grants-2015_11
Patent number
US09175032B2

Reaction notes

Loading…