Ethylene Glycol → HCID 67858042, compound

HRID 1613505Notes

Reaction equation

HRID 1613505 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH:8]=[C: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 12682296HCID 12682296, compound

Product 1

HCID 67858042HCID 67858042, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

2-Butyl-4-oxocyclohex-2-ene carboxylic acid ethyl ester (9.05 g; 40 mmole), ethyleneglycol (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-a8b64a63c49448feac0b5002f67d688c
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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