Benzyl Alcohol → HCID 12555046, compound

HRID 1957348Notes

Reaction equation

HRID 1957348 reaction equation
[OH:1][C:2]1[C:3](=[O:8])[C:4](=[O:7])[C:5]=1[OH:6].[CH2:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21](S(O)(=O)=O)=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH2:9]([O:7][C:4]1[C:5](=[O:6])[C:2](=[O:1])[C:3]=1[O:8][CH2:28][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 17913Squaric acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 12555046HCID 12555046, compoundYield 566.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,4-Dihydroxy-3-cyclobutene-1,2-dione (2.0 g, 17 mmol), benzyl alcohol (5.0 mL, 5.2 g, 48 mmol), and p-toluenesulfonic acid monohydrate (170 mg, 0.9 mmol) were slurried in toluene (20 mL), and heated under reflux with a Dean-Stark trap for 3 days. The insoluble material was filtered off, and the filtrate was diluted with ether (100 mL), washed with 2× with saturated aqueous NaHCO3 solution and brine, dried over Na2 SO4, filtered and concentrated to a crude residue. The crude product was purified by chromatography eluting with 4:1 hexane-EtOAc to give the title compound (1.5 g, 29%) as an oil which slowly solidified on standing. MS (FAB+) m/e 312 (M+NH3 +H)+.

Workup

  1. temperatureheated
  2. temperatureunder reflux with a Dean-Stark trap for 3 days
  3. filtrationThe insoluble material was filtered off
  4. additionthe filtrate was diluted with ether (100 mL)
  5. washwashed with 2× with saturated aqueous NaHCO3 solution and brine
  6. customdried over Na2 SO4
  7. filtrationfiltered
  8. concentrationconcentrated to a crude residue
  9. customThe crude product was purified by chromatography
  10. washeluting with 4:1 hexane-EtOAc

Sources & evidence

ORD record
ord-59af4239c94447e4957fffac24213031
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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