Ethylene Glycol → HCID 22320912, compound

HRID 1803217Notes

Reaction equation

HRID 1803217 reaction equation
S(=O)(=O)(O)O.[O:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[CH2:20](O)[CH2:21][OH:22].COC(OC)OC.C([O-])(O)=O.[Na+]>ClCCl>[C:14]1([C:7]2([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[O:22][CH2:21][CH2:20][O:6]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 73914delta-Oxobenzenepentanoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 22320912HCID 22320912, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step AAH (1): Concentrated sulfuric acid (0.200 mL, 3.75 mmol) was added to a mixture of 5-oxo-5-phenylpentanoic acid (4.0 g, 20.81 mmol), ethylene glycol (6.96 mL, 125 mmol), and trimethylorthoformate (6.90 mL, 62.4 mmol) in dichloromethane (40 mL) at it under nitrogen. The mixture was stirred at it for 16 h. Solid NaHCO3 (2.0 g) was carefully added. The resulting mixture was concentrated in vacuo. The residue was taken up in methanol (50 mL) and the vessel was placed in a it water bath. Aqueous 50% NaOH (5 mL) was slowly added and the mixture was stirred at for 16 h. The mixture was concentrated in vacuo (to remove methanol) and the resulting aqueous layer was neutralized to pH 2. The aqueous layer was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was crystallized from diethyl ether to afford 4-(2-phenyl-1,3-dioxolan-2-yl)butanoic acid (850 mg, 17% yield) which was contained with a significant portion of 5-oxo-5-phenylpentanoic acid. LC-MS (M+H)+ 235.1.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. additionAqueous 50% NaOH (5 mL) was slowly added
  3. stirringthe mixture was stirred at for 16 h
  4. concentrationThe mixture was concentrated in vacuo (to remove methanol)
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-b61f585dc27041c3b4f17fb17dd701da
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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