p-Toluenesulfonic acid → HCID 21532240, compound

HRID 1657948Notes

Reaction equation

HRID 1657948 reaction equation
[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH2:7](O)/[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[C:1]([O:6][CH2:7]/[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6590Isobutyric AcidHCID 53649412-Nonen-1-ol, (2E)-

Product 1

HCID 21532240HCID 21532240, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Isobutyric acid (22.0 g, 0.25 mole), trans-2-nonen-1-ol (44.3 g, 0.25 mole), xylene (100 ml) and p-toluenesulfonic acid are heated to 145°C. The solution is refluxed for 5 minutes and 4.5 ml water is collected by distillation. The reaction mixture is cooled and first washed with water followed by 5% sodium carbonate. The washed solution is dried over sodium sulfate and distilled to yield 34.1 g of trans-2-nonenyl isobutyrate, b.p. 87° - 88°C/0.5 mm. An analytical sample is obtained for taste evaluation using gas chromatography.

Workup

  1. temperatureThe solution is refluxed for 5 minutes
  2. distillation4.5 ml water is collected by distillation
  3. temperatureThe reaction mixture is cooled
  4. washfirst washed with water
  5. dry with materialThe washed solution is dried over sodium sulfate
  6. distillationdistilled

Sources & evidence

ORD record
ord-2b96c6d450a2449f88f902eee705e5d2
Source dataset
uspto-grants-1976_06
Patent number
US03962321

Reaction notes

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