Ethylene Glycol → HCID 12813211, compound

HRID 1448929Notes

Reaction equation

HRID 1448929 reaction equation
[CH2:1]([O:8][CH2:9][C:10](=[O:19])[CH2:11][CH2:12][CH:13]1[S:18][CH2:17][CH2:16][CH2:15][S:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20](O)[CH2:21][OH:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:1]([O:8][CH2:9][C:10]1([O:22][CH2:21][CH2:20][O:19]1)[CH2:11][CH2:12][CH:13]1[S:18][CH2:17][CH2:16][CH2:15][S:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 13151117HCID 13151117, compound

Product 1

HCID 12813211HCID 12813211, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Treatment of 1-benzyloxy-4-(1,3-dithian-2-yl)-butan-2-one (89.8 g) in benzene (3.5 l) with distilled ethylene glycol (220 ml) and p-toluenesulfonic acid (11.7 g) at reflux temperature in a Dean-Stark apparatus for 18 hours gives a mixture which is concentrated to 500 ml in vacuo and allowed to stir for one hour. After the addition of sodium carbonate (10 g), the mixture is then partitioned between ether (300 ml) and brine (300 ml). The aqueous phase is extracted with ether (600 ml) and the combined extracts are washed with 0.05% sodium carbonate (1.2 l), filtered through phase-separating paper and dried (sodium sulfate). The solvent is removed in vacuo to give a residue (102.15 g; 99%). A 200 mg portion of the residue is purified on Quantagram PQ1F plates (chloroform) to give 1-benzyloxy-2,2-ethylenedioxy-4-(1,3-dithian-2-yl)-butane (180 mg); ir (neat) C=O absent; nmr (CDCl3,δ ) 1.92 (m, 6H, CCH2CH2CH and ##STR13## 2.83 (m, 4H, SCH2CH2CH2S), 3.37 ##STR14## 3.93 ##STR15## 4.55 (s, 2H, φCH2O), 7.28 (s, 5H, φCH2O).

Workup

  1. customgives a mixture which
  2. concentrationis concentrated to 500 ml in vacuo
  3. additionAfter the addition of sodium carbonate (10 g)
  4. customthe mixture is then partitioned between ether (300 ml) and brine (300 ml)
  5. extractionThe aqueous phase is extracted with ether (600 ml)
  6. washthe combined extracts are washed with 0.05% sodium carbonate (1.2 l)
  7. filtrationfiltered
  8. customthrough phase-separating paper
  9. dry with materialdried (sodium sulfate)
  10. customThe solvent is removed in vacuo
  11. customto give a residue (102.15 g; 99%)
  12. customA 200 mg portion of the residue is purified on Quantagram PQ1F plates (chloroform)

Sources & evidence

ORD record
ord-600a7cc0c5c74e3aa076756c3d5c3592
Source dataset
uspto-grants-1980_02
Patent number
US04188328

Reaction notes

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