Ethylene Glycol → HCID 67858042, compound

HRID 1087979Notes

Reaction equation

HRID 1087979 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][C@@H:7]1[CH2:13][CH2:14][CH2:15][CH3:16])=[O:5])[CH3:2].[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1.C(OCC)C>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C:9]2([O:19][CH2:18][CH2:17][O:12]2)[CH2:8][C@H:7]1[CH2:13][CH2:14][CH2:15][CH3:16])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 54298689HCID 54298689, compound

Product 1

HCID 67858042HCID 67858042, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

cis-2-Butyl-4-oxocyclohexane carboxylic acid ethyl ester (9.0 g; 40 mmole), ethylene glycol (2.73 g; 44 mmole) and p-toluenesulphonic acid (100 mg) were refluxed in benzene 80 ml) using a Dean-Stark water trap. After 12 hours the mixture was cooled, diluted with diethyl ether and washed with saturated aqueous sodium bicarbonate followed by water. Drying over MgSO4 and evaporation gave a liquid (10.80 g; 100%) which was pure enough to use directly. Found: C, 66.71; H, 9.79. C15H26O4 requires C, 66.64; H, 9.69%.

Workup

  1. temperatureAfter 12 hours the mixture was cooled
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialDrying over MgSO4 and evaporation
  4. customgave a liquid (10.80 g; 100%) which

Sources & evidence

ORD record
ord-79175776ab2d4a09958cbf21c1607596
Source dataset
uspto-grants-1990_10
Patent number
US04960792

Reaction notes

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