Methyl 7-phthalimidohept-5-ynoate → 7-Phthalimidohept-5-ynoic Acid

HRID 358619Notes

Reaction equation

HRID 358619 reaction equation
[C:1]1(=[O:21])[N:5]([CH2:6][C:7]#[C: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>Cl.CC(C)=O.O>[C:4]1(=[O:16])[N:5]([CH2:6][C:7]#[C: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 20066955Methyl 7-phthalimidohept-5-ynoate

Product 1

HCID 154705147-Phthalimidohept-5-ynoic AcidYield 81.2%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

Methyl 7-phthalimidohept-5-ynoate (1.45 g) was dissolved in a mixture of concentrated hydrochloric acid (7.3 ml), acetone (30 ml) and water (14.6 ml) and the resulting solution was heated at reflux for 3.5 hours. The solution was cooled and then poured into water (175 ml). The precipitate was collected by filtration and recrystallised from ethanol-water to give the title compound (1.12 g) m.p. 120°-122° C.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 3.5 hours
  3. temperatureThe solution was cooled
  4. filtrationThe precipitate was collected by filtration
  5. customrecrystallised from ethanol-water

Sources & evidence

ORD record
ord-d5c0e32b8e5c4f339814a1b6d66005ad
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Reaction notes

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