Benzyl Alcohol → HCID 12798024, compound

HRID 1106020Notes

Reaction equation

HRID 1106020 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:17](O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([O:13][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 2941143HCID 2941143, compound

Product 1

HCID 12798024HCID 12798024, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 80.1 g of 2-(4-nitrophenyl)-3-methylbutanoic acid, 150 ml of benzyl alcohol, 75 ml of toluene and 2 g of p-toluenesulfonic acid monohydrate was boiled under reflux, with azeotropic removal of water, for 10 hours. The toluene and excess benzyl alcohol were removed in vacuum, and the residual oil was dissolved in butyl chloride. The butyl chloride solution was washed with 6% potassium carbonate three times (acidification of the carbonate extract precipitated 5.2 g of the starting carboxylic acid), water and saturated brine. The dried (MgSO4) butyl chloride solution was evaporated to a residual oil. The oil was vacuum distilled, the bulk of it boiling at 197°-200°/0.3 Torr, providing 99 g of 2-(4-nitrophenyl)-3-methylbutanoic acid, benzyl ester as a yellow oil.

Workup

  1. customThe toluene and excess benzyl alcohol were removed in vacuum
  2. dissolutionthe residual oil was dissolved in butyl chloride
  3. washThe butyl chloride solution was washed with 6% potassium carbonate three times (acidification of the carbonate
  4. extractionextract
  5. customprecipitated 5.2 g of the starting carboxylic acid), water and saturated brine
  6. dry with materialThe dried (MgSO4) butyl chloride solution
  7. customwas evaporated to a residual oil
  8. distillationdistilled

Sources & evidence

ORD record
ord-39902effd7d2456fa468e94ec9890ed7
Source dataset
uspto-grants-1982_01
Patent number
US04311696

Reaction notes

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