Ethylene Glycol → 5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoic acid

HRID 1108382Notes

Reaction equation

HRID 1108382 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].C[C:6]1[CH:7]=[CH:8]C(S(O)(=O)=O)=[CH:10][CH:11]=1.C1(C)C=CC=CC=1.[OH-].[Na+].CC[O:27][C:28]([CH3:30])=[O:29]>CCOCC.O>[CH3:10][C:11]1([CH2:6][CH2:7][CH2:8][CH2:30][C:28]([OH:27])=[O:29])[O:4][CH2:1][CH2:2][O:3]1

Participants

8

Reactant 5

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide

Product 1

HCID 154537565-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of ketone 2-1 (18 g, 105 mmol), ethylene glycol (3.2 ml, 110 mmol), p-TSA (50 mg, 0.2713 mmol) and toluene (300 mL) was heated to reflux with azeotropic removal of water for 24 hours. The reaction mixture was diluted with EtOAc and then washed with sat. NaHCO3, brine, dried (MgSO4), and concentrated. The residue was dissolved in EtOH (200 ml) and then treated with 1N NaOH (120 ml, 120 mmol). After 2 h, the reaction was poured into 600 mL 2:1 Et2O/10% KHSO4. The organic portion was separated, washed with brine, dried (MgSO4) and concentrated to give acid 2-2 as a colorless oil.

Workup

  1. temperaturewas heated
  2. washwashed with sat. NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in EtOH (200 ml)
  6. customThe organic portion was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-386c4d941997456fbfd8463efa96c33b
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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