Ethylene Glycol → Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate

HRID 1948089Notes

Reaction equation

HRID 1948089 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:13](O)[CH2:14][OH:15].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-ethoxycarbonyl-cyclohexanone (11.0 g, 64.6 mmol), 1,2-ethanediol (6.02 g, 96.9 mmol), and p-TsOH.H2O (620 mg, 3.2 mmol) in toluene (60 mL) was refluxed using a Dean-Stark to collect water overnight. The mixture was cooled to rt, then quenched with sat. aq. NaHCO3 (30 mL) and diluted with EtOAc (100 mL). The organic layer was washed with brine (30 mL), and dried over anhydrous sodium sulfate. The solvents were evaporated under reduced pressure to give the title compound as a light-yellow oil. 13.8 g, 100% yield. The material was used in next step without further purification. 1H NMR (CDCl3): 1.25 (t, J=7.1 Hz, 3H), 1.52-1.60 (m, 2H), 1.76-1.83 (m, 4H), 1.92-1.97 (m, 2H), 2.34 (m, 1H), 3.95 (s, 4H), 4.13 (q, J=7.1 Hz, 2H).

Workup

  1. temperaturewas refluxed
  2. customto collect water overnight
  3. customquenched with sat. aq. NaHCO3 (30 mL)
  4. additiondiluted with EtOAc (100 mL)
  5. washThe organic layer was washed with brine (30 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-fbb98fcffd354ad3abb512f2c20ea552
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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