Ethylene Glycol → HCID 59537271, compound

HRID 1781970Notes

Reaction equation

HRID 1781970 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:18](O)[CH2:19][OH:20].CC1C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:18]1[CH2:19][O:20][C:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[O:1]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 3017756Ethyl 3-oxododecanoate

Product 1

HCID 59537271HCID 59537271, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The mixture of ethyl 3-oxododecanoate (1.456 g, ca. 5 mmol), ethylene glycol (2.78 mL, 50 mmol) and a catalytic amount of p-TsOH (95 mg, 0.5 mmol) in benzene (50 mL) was heated to 110° C. under an argon atmosphere overnight. The solvent was removed, and the residue was diluted with 50 mL ethyl acetate. The solution was washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL), and the organic phase was dried over MgSO4 and concentrated. The residue was purified by flash chromatography (hexane/EtOAc 8:1, Rf=0.21) to give ethyl 3,3-ethylenedioxydodecanoate (1.131 g, 3.95 mmol) in 79% overall yield for the above two steps. 1H NMR (500 MHz, CDCl3) δ 0.88 (t, J=7 Hz, 3H), 1.20-1.44 (m, 17H), 1.76-1.82 (m, 2H), 2.65 (s, 2H), 3.94-4.04 (m, 4H), 4.16 (q, J=7 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 14.1, 22.6, 23.4, 29.22, 29.43, 29.48, 29.62, 31.8, 37.7, 42.5, 60.4, 65.0, 109.4, 169.5.

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with 50 mL ethyl acetate
  3. washThe solution was washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (hexane/EtOAc 8:1, Rf=0.21)

Sources & evidence

ORD record
ord-bccd1606f68f46538243c62ad1d15035
Source dataset
uspto-grants-2009_03
Patent number
US07498292B2

Reaction notes

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