Sodium hydride → Pentanoic acid, 3-acetyl-4-oxo-, phenylmethyl ester

HRID 615020Notes

Reaction equation

[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[H-].[Na+].[CH2:10]([O:17][C:18](=[O:21])[CH2:19]Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:17][C:18](=[O:21])[CH2:19][CH:4]([C:5](=[O:7])[CH3:6])[C:1](=[O:3])[CH3:2])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 31261Acetylacetone

HCID 62576Benzyl bromoacetate

Product 1

HCID 54450814Pentanoic acid, 3-acetyl-4-oxo-, phenylmethyl esterYield 51%

Procedure

10 grams acetylacetone were reacted with 5 grams of a 50% suspension of sodium hydride in paraffin oil and with 25 grams bromoacetic acid-benzylester in accordance with a procedure analogous to that set out in Example (2b). 3,3-diacetyl-propionic acid-benzylester having a Kp0.005 of 126°-128° C. was obtained. This substance was further reacted with phenylhydrazine by a procedure analogous to that set out in Example (2c). 3,5-dimethyl-1-phenyl-pyrazol-4-acetic acid-benzylester, having a Kp0.001 of 205°-209° C., was obtained in a yield of 51%.

Sources & evidence

ORD record: ord-dbd05169129b4b61b6f790bfc49f5b7f
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04146721

Reaction notes

Loading…