Malonic Acid → 3-[4-(Dodecyloxy)phenyl]prop-2-enoic acid

HRID 850240Notes

Reaction equation

C(O)(=O)CC(O)=O.[CH:8]1[C:13](/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])=[CH:12][CH:11]=[C:10]([OH:19])[CH:9]=1.[CH2:20](Br)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>>[CH2:31]([O:19][C:10]1[CH:11]=[CH:12][C:13]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])=[CH:8][CH:9]=1)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20]

Participants

Reactant 3

HCID 867Malonic Acid

HCID 89191-Bromododecane

HCID 637542P-Coumaric Acid

Product 1

HCID 542773203-[4-(Dodecyloxy)phenyl]prop-2-enoic acid

Procedure

4-Dodecyloxycinnamic acid is prepared by generally known processes by condensation of a 4-alkoxybenzaldehyde with malonic acid or by reaction of coumaric acid with dodecyl bromide. The colourless crystals have a melting point of 158-159° C. The corresponding acid chloride is obtained therefrom virtually quantitatively by reaction with oxalyl chloride in benzene (18 hours, room temperature).

Sources & evidence

ORD record: ord-9f1adb3e9b0b4c3fb743eb402fe7abc4
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017556

Reaction notes

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