Benzyl Alcohol → HCID 19810564, compound

HRID 373646Notes

Reaction equation

HRID 373646 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](S(O)(=O)=O)=[CH:6][CH:7]=1.[OH2:12].[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1C=CC=CC=1>[CH2:1]([CH:16]([CH2:15][CH2:14][CH2:13][OH:20])[C:17]([O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 19810564HCID 19810564, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The methyl ester (4 g, 18 mmol) from the above reaction was dissolved in 10 ml of benzyl alcohol and 50 ml of Benzene. After adding TsOH.H2O (0.5 g, 2.63 mmol), the contents were heated under reflux for 2 h. Once the required amount of H2O had been collected, the solution was concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, Hexane-AcOEt, 3:1) which gave 3.8 g (71%) of the title compound: 7.40-7.10 (m,10H), 5.03 (s,2H), 3.57 (t,J=6Hz,2H), 3.00-2.60 (m,≈4H), and 1.80-1.40 (m,4H).

Workup

  1. temperaturethe contents were heated
  2. temperatureunder reflux for 2 h
  3. customOnce the required amount of H2O had been collected
  4. concentrationthe solution was concentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica gel, Hexane-AcOEt, 3:1) which

Sources & evidence

ORD record
ord-ac24f4e6859a4b5d92ab8afa3093b2cd
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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