Malonic Acid → 3-(4-Heptylphenyl)prop-2-enoyl chloride

HRID 460751Notes

Reaction equation

HRID 460751 reaction equation
C(C1C=CC(C=O)=CC=1)CCCCCC.C(O)(=O)CC(O)=O.[CH2:23]([C:30]1[CH:40]=[CH:39][C:33]([CH:34]=[CH:35][C:36](O)=[O:37])=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].S(Cl)([Cl:43])=O>N1CCCCC1.CCOCC.N1C=CC=CC=1>[CH2:23]([C:30]1[CH:40]=[CH:39][C:33]([CH:34]=[CH:35][C:36]([Cl:43])=[O:37])=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

8

Reactant 4

HCID 867Malonic AcidHCID 24386Thionyl ChlorideHCID 109216344-HeptylbenzaldehydeHCID 53734772p-n-Heptylcinnamic acid

Product 1

HCID 541980353-(4-Heptylphenyl)prop-2-enoyl chloride

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

8.8 G. of p-n-heptylbenzaldehyde and 8.74 g. of malonic acid are dissolved in 7 ml. of absolute pyridine, treated with 8 drops of piperidine and heated at 90°-100° C. for 68 hours. The mixture is then taken up in ether and washed with dilute hydrochloric acid. After recrystallization from ether/hexane, there are obtained 7.5 g. of p-n-heptylcinnamic acid having a melting point of 121°-122° C. and a clearing point of 150°-153° C. 8.2 G. of this acid are boiled at reflux in 120 ml. of thionyl chloride for 30 minutes. The excess thionyl chloride is removed by distillation, the residue taken up three times in absolute toluene, concentrated and dried. The p-n-heptylcinnamic acid chloride obtained can be used in the process directly.

Workup

  1. temperatureheated at 90°-100° C. for 68 hours
  2. washwashed with dilute hydrochloric acid
  3. customAfter recrystallization from ether/hexane, there
  4. customare obtained 7.5 g
  5. customa clearing point of 150°-153° C
  6. temperatureat reflux in 120 ml
  7. customThe excess thionyl chloride is removed by distillation
  8. concentrationconcentrated
  9. customdried

Sources & evidence

ORD record
ord-5f90ec3a2e5b4aa7b1e6ba6e6613cfcf
Source dataset
uspto-grants-1977_12
Patent number
US04061587

Reaction notes

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