Hydrochloric Acid → HCID 14589900, compound

HRID 1497012Notes

Reaction equation

HRID 1497012 reaction equation
[C:1]1([CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[C:13]([O:15]CC)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 20628704HCID 20628704, compound

Product 1

HCID 14589900HCID 14589900, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

(2E,4E)-Ethyl 7-phenylhepta-2,4-dienoate (355 mg) was dissolved in methanol (5 ml). 2M aqueous sodium hydroxide (1.002 ml) was added and the resulting suspension was heated to 60° C. The reaction mixture was stirred for 2 h. After cooling to room temperature the mixture was acidified with 1M aqueous HCl and extracted three times with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated to yield an off-white solid. The residue was taken up with 1M aqueous NaOH (10 ml) and extracted with Et2O. The aqueous layer was acidified with 2M aqueous HCl and extracted twice with EtOAc. The combined EtOAc layer was washed with brine, dried over Na2SO4 and concentrated.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto yield an off-white solid
  7. extractionextracted with Et2O
  8. extractionextracted twice with EtOAc
  9. washThe combined EtOAc layer was washed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-bf199fd1368249eb807738924d83a4cb
Source dataset
uspto-grants-2015_12
Patent number
US09199948B2

Reaction notes

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