Toluene → 3-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

HRID 1856376Notes

Reaction equation

HRID 1856376 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1([CH3:18])[CH:12]2[C:13]3([CH3:17])[O:16][CH:14]3[CH2:15][CH:10]1[CH2:11]2.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(O)(=O)C>[CH3:11][C:12]1[C:9]([CH3:8])([CH3:18])[CH:10]([CH2:15][CH:14]=[O:16])[CH2:17][CH:13]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 5234Sodium ChlorideHCID 91508alpha-Pinene oxideHCID 516892Sodium Bicarbonate

Product 1

HCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The reaction mass is then transferred to a 5 liter flask and 2145 grams of toluene are added. Alpha-pinene epoxide (1086 grams, 7.1 moles) is then added over a period of 1 hour while maintaining the reaction mass temperature below 53° C. using dry-ice/isopropanol bath in order to control exotherm. The reaction mass is then stirred for an additional 2 hours after addition is complete. The reaction mass is then intimately admixed with a 10% acetic acid solution to a pH of 4.3 followed by neutralization with sodium bicarbonate and sodium chloride solutions. The toluene is then recovered and the reaction mass crude material is "rush over" distilled whereby 785.3 grams of product is collected. (Chemical yield=74%). The rush over distillation fractions are collected using a 2 inch rush over column packed with saddle stones yielding the following fractions:

Workup

  1. customThe reaction mass is then transferred to a 5 liter flask
  2. temperaturewhile maintaining the reaction mass temperature below 53° C.
  3. additionafter addition
  4. customThe toluene is then recovered
  5. distillationdistilled whereby 785.3 grams of product
  6. customis collected
  7. distillationThe rush over distillation fractions
  8. customare collected
  9. customyielding the following fractions

Sources & evidence

ORD record
ord-5616ea753c4049eabb469532104f5792
Source dataset
uspto-grants-1980_08
Patent number
US04219451

Reaction notes

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