Ethylene Glycol → HCID 13588848, compound

HRID 256198Notes

Reaction equation

HRID 256198 reaction equation
C1CCCCC1.[CH2:7]([OH:10])[CH2:8][OH:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:32][CH:33]([N+:47]([O-:49])=[O:48])[CH2:34][CH2:35][C:36](=O)[CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]>C1C=CC=CC=1>[CH2:7]1[O:10][C:34]([CH2:35][CH2:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)([CH:33]([N+:47]([O-:49])=[O:48])[CH2:32][C:26]2[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:24]([O:23][CH3:22])[CH:25]=2)[O:9][CH2:8]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 8078CyclohexaneHCID 20164187HCID 20164187, compound

Product 1

HCID 13588848HCID 13588848, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 500 mL rb flask, 200 mL cyclohexane, 50 mL benzene, 15 g.(0.242 mole) ethylene glycol, 1.5 g p-toluene-sulfonic acid and 19 g (0.049 mole) of 1-(3,4-dimethoxyphenyl)-2-nitro-7-(4-methylphenyl)-5-heptanone were combined and refluxed 24 hours with a Dean-Stark trap. The cooled reaction mixture was poured into cold, sat'd. NaHCO3 and extracted with three 200 mL portions of ethyl acetate. The organic Layer was dried over MgSO4, filtered and concentrated. The residue was triturated with ether and ethyl acetate to give some solid (1.5 g) of mp 89°-91° C.

Workup

  1. temperaturerefluxed 24 hours with a Dean-Stark trap
  2. customThe cooled reaction mixture
  3. additionwas poured into cold, sat'd
  4. extractionNaHCO3 and extracted with three 200 mL portions of ethyl acetate
  5. dry with materialThe organic Layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with ether and ethyl acetate

Sources & evidence

ORD record
ord-90ff2dff5a2f4b1c9b7d4019aa03dde1
Source dataset
uspto-grants-1987_10
Patent number
US04701461

Reaction notes

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