Mesityl oxide → 3-Cyclohexene-1-carboxylic acid, 6,6-dimethyl-2-methylene-, ethyl ester

HRID 436716Notes

Reaction equation

HRID 436716 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.O=[C:11]([CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:12].C([O-])([O-])=O.[Na+].[Na+]>O>[CH2:5]=[C:3]1[CH:12]=[CH:11][CH2:13][C:14]([CH3:16])([CH3:15])[CH:2]1[C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 8858Mesityl oxideHCID 8868Ethyl AcetoacetateHCID 10340Sodium Carbonate

Product 1

HCID 1182003-Cyclohexene-1-carboxylic acid, 6,6-dimethyl-2-methylene-, ethyl esterYield 29.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

260 g of ethyl acetoacetate were mixed with 200 g of mesityl oxide and 200 g of trifluoroboro-etherate in a vessel cooled externally by water and ice in order to maintain the temperature of the mixture at about 0°-5°. The said mixture is maintained at this temperature for 3 days, poured then onto ice (800 g) and neutralized with about 400 g of Na2CO3. Then it was extracted with ether and, after the usual treatments of separation, washing and drying, the combined organic extracts were concentrated. Distillation of the residue (135 g) gave 115 g of the desired product, b.p. 85°-90°/0.1 Torr, which has a purity of 80% as shown by analysis by means of vapour phase chromatography. The product can subsequently be purified by redistillation.

Workup

  1. temperatureto maintain the temperature of the mixture at about 0°-5°
  2. temperatureThe said mixture is maintained at this temperature for 3 days
  3. additionpoured
  4. extractionThen it was extracted with ether
  5. customafter the usual treatments of separation
  6. washwashing
  7. customdrying
  8. concentrationthe combined organic extracts were concentrated
  9. distillationDistillation of the residue (135 g)

Sources & evidence

ORD record
ord-670a007fb6e4455b9150b335f7b46cb2
Source dataset
uspto-grants-1977_06
Patent number
US04028278

Reaction notes

Loading…