Ethylene Glycol → (S)-6-Ethyl-1,4-dioxaspiro[4.5]decane-6-propanoic Acid, 2-Hydroxyethyl Ester

HRID 247649Notes

Reaction equation

HRID 247649 reaction equation
[CH2:1]([C@@:3]1([CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9])[CH3:2].[CH2:15]([OH:18])[CH2:16]O.[C:19]1([CH3:29])C=CC(S(O)(=O)=O)=CC=1.[OH2:30]>C1(C)C=CC=CC=1>[CH2:1]([C@@:3]1([CH2:10][CH2:11][C:12]([O:14][CH2:16][CH2:15][OH:18])=[O:13])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]21[O:30][CH2:19][CH2:29][O:9]2)[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 54536642(S)-1-Ethyl-2-oxocyclohexanepropanoic Acid

Product 1

HCID 56993252(S)-6-Ethyl-1,4-dioxaspiro[4.5]decane-6-propanoic Acid, 2-Hydroxyethyl Ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

(S)-1-Ethyl-2-oxocyclohexanepropanoic acid (605 g), and ethylene glycol (14.6 mol, 906 g, 814 mL) were refluxed in 1.5 L of toluene containing 10 g of p-toluenesulfonic acid with azeotropic removal of water. After 56 hours, water stopped coming off. The reaction was diluted with 1 L of toluene and washed with water (2×500 mL), saturated sodium bicarbonate (aq) (2×500 mL), and brine (500 mL). Drying (magnesium sulfate) and concentration afforded 942 g of clear yellow oil which was used as in the next step.

Workup

  1. washwashed with water (2×500 mL), saturated sodium bicarbonate (aq) (2×500 mL), and brine (500 mL)
  2. customDrying
  3. concentration(magnesium sulfate) and concentration

Sources & evidence

ORD record
ord-05c06058a7df4a91b738f4f9f58d31d2
Source dataset
uspto-grants-1987_11
Patent number
US04709048

Reaction notes

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