Ethylene Glycol → HCID 57166565, compound

HRID 256394Notes

Reaction equation

HRID 256394 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[S:9](=[O:14])(=[O:13])[CH2:8][CH2:7][CH2:6]2)=[O:2].C1(C)C=CC=CC=1.[CH2:22](O)[CH2:23][OH:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[O:2]1[CH2:22][CH2:23][O:24][CH:1]1[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[S:9](=[O:14])(=[O:13])[CH2:8][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 13728730109210-01-7

Product 1

HCID 57166565HCID 57166565, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3.0 g (14.3 mmole) 6-formyl-1,1dioxothiachroman and 140 ml toluene was added 15.9 ml ethylene glycol and 0.66 g (3.5 mmole) p-toluenesulfonic acid hydrate. The mixture was heated at reflux for 18 hours or until no further water was collected in the attached water separator (Dean-Stark trap). The reaction mixture was cooled, diluted with ethyl acetate, washed with water, sodium bicarbonate, water again, brine and dried (MgSO4). Evaporation of solvent in vacuo gave 3.73 g of residual oil which solidified on standing. Mass spectrum (m/e): 254 (M+).

Workup

  1. temperatureThe mixture was heated
  2. customwas collected in the attached water separator (Dean-Stark trap)
  3. temperatureThe reaction mixture was cooled
  4. additiondiluted with ethyl acetate
  5. washwashed with water, sodium bicarbonate, water again
  6. dry with materialbrine and dried (MgSO4)
  7. customEvaporation of solvent in vacuo

Sources & evidence

ORD record
ord-90ab59e28b6944999f0abd62c09bedaa
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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