Hydrochloric Acid → 4-(Tert-butyl)cinnamic acid

HRID 1983842Notes

Reaction equation

HRID 1983842 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[C:8]([C:12]1[CH:19]=[CH:18][C:15](C=O)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].N1CCCCC1.Cl>N1C=CC=CC=1>[C:8]([C:12]1[CH:19]=[CH:18][C:15](/[CH:1]=[CH:2]/[C:3]([OH:5])=[O:4])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 703244-tert-Butylbenzaldehyde

Product 1

HCID 7248394-(Tert-butyl)cinnamic acidYield 48,051.898%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

19.20 g (0.185 mol) of malonic acid were dissolved in pyridine (33 ml) and stirred for 15 minutes at RT. 25.00 g (0.154 mmol) of para-tert.-butylbenzaldehyde and 1.50 ml (0.020 mol) of piperidine were then added. The reaction mixture was heated for 8 hours at 100° C., with stirring. After pouring the reaction solution into a mixture of concentrated hydrochloric acid and ice, stirring was continued for a further two hours at room temperature. The resulting precipitate was filtered out with suction. Recrystallisation of the precipitate from methanol yielded 15.20 g (0.074 mol, 48% of theory) of para-tert.-butyl-trans-cinnamic acid.

Workup

  1. temperatureThe reaction mixture was heated for 8 hours at 100° C.
  2. stirringwith stirring
  3. additionAfter pouring the reaction solution
  4. stirringstirring
  5. waitwas continued for a further two hours at room temperature
  6. filtrationThe resulting precipitate was filtered out with suction
  7. customRecrystallisation of the precipitate from methanol

Sources & evidence

ORD record
ord-c88b43ec9efa4f6eb09e153bca63ea64
Source dataset
uspto-grants-2009_06
Patent number
US07541495B2

Reaction notes

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