Malonic Acid → 2-Methylbenzylidenemalonic acid

Reaction equation

[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([OH:16])(=[O:15])[CH2:11][C:12]([OH:14])=[O:13]>>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:11]([C:10]([OH:16])=[O:15])[C:12]([OH:14])=[O:13]

Participants

Reactant 2

HCID 867Malonic Acid

HCID 107222-Methylbenzaldehyde

Product 1

HCID 100588002-Methylbenzylidenemalonic acid

Conditions

Temperature: 90 °C

Procedure

Combine 2-methylbenzaldehyde (39.6 g, 0.33 mol) and malonic acid (34.3 g, 0.33 mol). Heat at 90° C. for one hour, add 3.9 g of the aldehyde, and heat 6 hr. at 90°. Allow to cool, partition between diethyl ether and 1N NaOH, acidify the aqueous layer, filter off the solid, wash and dry to give the title compound as a beige solid, m.p. 197°-200°.

Workup

temperatureheat 6 hr
customat 90°
temperatureto cool
custompartition between diethyl ether and 1N NaOH
filtrationfilter off the solid
washwash
customdry

Sources & evidence

ORD record: ord-1868c05858394c2c9370ed101e8006ec
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04929641

Reaction notes

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