Benzene → 1,3-Cyclohexadiene-1-carboxylic acid, 2,6,6-trimethyl-, ethyl ester

HRID 436719Notes

Reaction equation

HRID 436719 reaction equation
[CH3:1][C:2]1[CH:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]([CH3:9])([CH3:8])[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>CCCCC>[CH3:1][C:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 118199Ethyl 2,6,6-trimethylcyclohexa-2,4-diene-1-carboxylate

Product 1

HCID 1182011,3-Cyclohexadiene-1-carboxylic acid, 2,6,6-trimethyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

A mixture of 2.0 g of 2,6,6-trimethyl-1-ethoxycarbonyl-2,4-cylohexadiene [prepared according to the process indicated in Example 1], 100 mg of p-toluenesulphonic acid and 25 ml of anhydrous benzene were refluxed for 4 hours in a nitrogen atmosphere. The resulting solution was diluted with pentane, washed with a 5 % solution of sodium bicarbonate, then with water, and then dried over Na2SO4 and concentrated.

Workup

  1. customprepared
  2. temperaturewere refluxed for 4 hours in a nitrogen atmosphere
  3. washwashed with a 5 % solution of sodium bicarbonate
  4. dry with materialwith water, and then dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-062c75b6511c45838ce5dacbd2b6898a
Source dataset
uspto-grants-1977_06
Patent number
US04028278

Reaction notes

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