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

HRID 1010526Notes

Reaction equation

HRID 1010526 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].C(OC)(OC)OC.[CH2:20](O)[CH2:21][OH:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl.C(N(CC)CC)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]2([O:22][CH2:21][CH2:20][O:12]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A mixture that consists of 7.35 g of 4-oxocyclohexylcarboxylic acid ethyl ester, 28 ml of trimethyl orthoformate, 64 ml of ethylene glycol and 100 mg of p-toluenesulfonic acid in 120 ml of dichloromethane is stirred for 12 hours at 25° C. Then, 2 ml of triethylamine is added. It is washed with saturated sodium bicarbonate solution and then with saturated sodium chloride solution, dried on sodium sulfate, and concentrated by evaporation in a vacuum. The crude product that is obtained is purified by column chromatography on silica gel. 9.22 g of product is obtained.

Workup

  1. washIt is washed with saturated sodium bicarbonate solution
  2. dry with materialwith saturated sodium chloride solution, dried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customThe crude product that is obtained
  5. customis purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a0ad4cc32f2c40c496bb88d69366275d
Source dataset
uspto-grants-2011_07
Patent number
US07977325B2

Reaction notes

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