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

HRID 1477182Notes

Reaction equation

HRID 1477182 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].CCOCC>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 3283Diethyl EtherHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl-4-oxocyclohexane carboxylate (28.9 g, 169 mmol), ethylene glycol (36.7 g, 33.0 mL, 592 mmol) and p-toluol sulphonic acid (380 mg, 2.0 mmol) in toluol (90 mL) was stirred overnight at room temperature. The reaction solution was poured into ether (150 mL) and washed with water and 5% sodium hydrogencarbonate solution (150 mL each). The organic phase was dried with sodium sulphate and concentrated to low volume in a vacuum. Since the raw product (26.8 g) was obtained in pure form, it could be directly converted further.

Workup

  1. washwashed with water and 5% sodium hydrogencarbonate solution (150 mL each)
  2. dry with materialThe organic phase was dried with sodium sulphate
  3. concentrationconcentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-e6efa1d1fe8a411aad47040e6566f07b
Source dataset
uspto-grants-2016_08
Patent number
US09403767B2

Reaction notes

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