Toluene → HCID 23702061, compound

HRID 1288589Notes

Reaction equation

HRID 1288589 reaction equation
[CH2:1]([C:4]([CH2:11][CH2:12][CH3:13])([CH2:8][CH2:9][CH3:10])[C:5]([OH:7])=[O:6])[CH2:2][CH3:3].C1(C)C=CC=CC=1.[OH-].[Na+:22]>CO>[CH2:11]([C:4]([CH2:1][CH2:2][CH3:3])([CH2:8][CH2:9][CH3:10])[C:5]([O-:7])=[O:6])[CH2:12][CH3:13].[Na+:22]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 1040672,2-Dipropylpentanoic acid

Product 1

HCID 23702061HCID 23702061, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flask equipped with a dropping-funnel and a mechanical strirrer were placed 30 g (0.161 mol) of pure tri-n-propylacetic acid prepared as described above and 75 g of toluene. The mixture was stirred until dissolution after which a hot solution of 6.45 g of sodium hydroxide in 30 g of methanol was added through the dropping-funnel. To the solution thus obtained was added 1 g of CECA WSL black after which the whole was refluxed for 1 hour while being stirred. The black was filtered off and the residual mixture was distilled by adding little-by-little through the dropping-funnel 88 g of toluene to prevent the mixture from forming a mass. Distillation was suspended when the temperature at the head of the column reached 105° C, after which the mixture was cooled to room-temperature. The precipitate which formed was centrifuged out and rinsed twice with 20 g of acetone. It was then dried in a rotatory evaporator at 80° C for 2 hours and then at 105° C under atmospheric pressure in a ventilated drying-oven for 4 hours. In this way, 30 g of sodium tri-n-propylacetate were obtained which represents a yield of 89.5%.

Workup

  1. customIn a flask equipped with a dropping-funnel
  2. customprepared
  3. additionwas added through the dropping-funnel
  4. customTo the solution thus obtained
  5. additionwas added 1 g of CECA WSL black after which the whole
  6. temperaturewas refluxed for 1 hour
  7. filtrationThe black was filtered off
  8. distillationthe residual mixture was distilled
  9. additionby adding little-by-little through the dropping-funnel 88 g of toluene
  10. customfrom forming a mass
  11. distillationDistillation
  12. customreached 105° C
  13. temperatureafter which the mixture was cooled to room-temperature
  14. customThe precipitate which formed
  15. washrinsed twice with 20 g of acetone
  16. customIt was then dried in a rotatory evaporator at 80° C for 2 hours

Sources & evidence

ORD record
ord-409f246f0988421594d0e102a8202a0e
Source dataset
uspto-grants-1976_10
Patent number
US03988472

Reaction notes

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