Hydrochloric Acid → p-n-Hexylcinnamic acid

HRID 1833752

Reaction equation

HRID 1833752 reaction equation
[CH2:1]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].Cl>N1CCCCC1.N1C=CC=CC=1>[CH2:1]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[CH:16][C:17]([OH:19])=[O:18])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 170813Benzaldehyde, 4-hexyl-

Product 1

HCID 53878923p-n-Hexylcinnamic acid

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

9.4 G. of p-n-hexylbenzaldehyde in 5 ml. of absolute pyridine are treated with 5.15 g. of malonic acid and 5 drops of piperidine. The mixture is then heated at 100° C. for 11 hours, subsequently poured on to cold aqueous hydrochloric acid and extracted with ether. The p-n-hexylcinnamic acid obtained after recrystallization of the crude product from hexane/ether has a melting point of 107°-109° C.

Workup

  1. extractionextracted with ether

Sources & evidence

ORD record
ord-511137de192940c4a23533203fb55e02
Source dataset
uspto-grants-1978_01
Patent number
US04066570

Linked notes

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