Sulfuric Acid → HCID 53641044, compound

HRID 1283177Notes

Reaction equation

HRID 1283177 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][C:8](=[O:13])[CH:7]=[C:6]1[CH3:14])=[O:4].C(OCC)(OCC)O[CH2:17][CH3:18].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH3:11])([CH3:12])[CH2:9][C:8]([O:13][CH2:17][CH3:18])=[CH:7][C:6]=1[CH3:14])=[O:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 68133032Methyl 2,6,6-trimethyl-4-oxo-2-cyclohexene-1-carboxylate

Product 1

HCID 53641044HCID 53641044, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

800 g. of crude 3,5,5-trimethyl-2-cyclohexen-1-on-4-carboxylic acid methyl ester prepared in Example 1, and 720 g. of triethyl orthoformate were mixed with 1.5 l. of anhydrous ethanol containing 4 ml. of sulfuric acid. After standing for 4 hours at room temperature, the dark blue solution was poured onto petroleum ether over a sodium bicarbonate solution. The ether layer was washed twice with water, dried over sodium sulfate, and concentrated by removing all of the ether solvent. The resulting dark residue was distilled over a vigreux column under high vacuum to yield 2,6,6-trimethyl-4-ethoxy-1,3-cyclohexadien-1-carboxylic acid methyl ester.

Workup

  1. washThe ether layer was washed twice with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customby removing all of the ether solvent
  5. distillationThe resulting dark residue was distilled over a vigreux column under high vacuum

Sources & evidence

ORD record
ord-ba5474e8b0c24fd4b3b9c051acdf46e3
Source dataset
uspto-grants-1976_08
Patent number
US03974181

Reaction notes

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