Methanol → HCID 23353913, compound

HRID 235198Notes

Reaction equation

HRID 235198 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:14][CH:13]=2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24]O>S(=O)(=O)(O)O>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:17]=2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 23353745HCID 23353745, compound

Product 1

HCID 23353913HCID 23353913, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a suspension of 2.10 g of 4-[4-(4-phenylbutyryl)phenyl]butyric acid in 15 ml of methanol, 0.1 ml of sulfuric acid was added, and the mixture was heated under reflux for 4 hours. After the reaction solution was removed under reduced pressure, the residue was dissolved in ethyl acetate and then washed successively with water, aqueous potassium carbonate and water. After the ethyl acetate layer was dried, the solvent was removed under reduced pressure. The residue was washed with isopropyl ether to yield 1.87 g of colorless crystals. Recrystallization from methanol gave colorless flakes, mp 61°~62° C.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 4 hours
  4. customAfter the reaction solution was removed under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed successively with water, aqueous potassium carbonate and water
  7. dry with materialAfter the ethyl acetate layer was dried
  8. customthe solvent was removed under reduced pressure
  9. washThe residue was washed with isopropyl ether

Sources & evidence

ORD record
ord-62ef74134130420db61d1550dd588db9
Source dataset
uspto-grants-1997_01
Patent number
US05597848

Reaction notes

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