Methyl (Z)-7-phthalimidohept-5-enoate → (Z)-7-Phthalimidohept-5-enoic Acid

HRID 358623Notes

Reaction equation

HRID 358623 reaction equation
[C:1]1(=[O:21])[N:5]([CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])[C:4](=[O:16])[C:3]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:2]12>CC(C)=O.Cl.O>[C:4]1(=[O:16])[N:5]([CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:1](=[O:21])[C:2]2=[CH:20][CH:19]=[CH:18][CH:17]=[C:3]12

Participants

5

Reactant 1

HCID 86744641Methyl (Z)-7-phthalimidohept-5-enoate

Product 1

HCID 67946768(Z)-7-Phthalimidohept-5-enoic AcidYield 80.9%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of methyl (Z)-7-phthalimidohept-5-enoate (1.56 g) in acetone (30 ml), concentrated hydrochloric acid (15 ml) and water (15 ml) was refluxed for 2.5 hours. Water (180 ml) was added and the solution was cooled. The precipitate was collected by filtration to give the title compound (1.2 g). m.p. 86°-88° C.

Workup

  1. temperaturethe solution was cooled
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2b262f54b69b4c24a4ef5f86f10f6fce
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Reaction notes

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