Sodium Carbonate → HCID 20197106, compound

HRID 652382Notes

Reaction equation

HRID 652382 reaction equation
[CH3:1][C:2]1([CH3:9])[C:7](=[O:8])[CH:6]=[CH:5][CH2:4][CH2:3]1.[CH3:10][C:11]([CH:13]=[CH:14][CH3:15])=[CH2:12].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:9])[CH2:3][CH2:4][CH:5]2[CH:6]([CH:14]([CH3:15])[CH:13]=[C:11]([CH3:12])[CH2:10]2)[C:7]1=[O:8]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 142381,3-Pentadiene, 2-methyl-HCID 117883026,6-Dimethyl-2-cyclohexen-1-one

Product 1

HCID 20197106HCID 20197106, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

124 G (1M) of 6,6-dimethyl-cyclohex-2-en-1-one, 200 ml of toluene and 10 ml of trifluoro-boro-etherate are placed under nitrogen atmosphere in a three-necked reaction vessel of 1000 ml capacity equipped with a thermometer and a stirrer. The mixture was cooled to 10° and 2-methyl-penta-1,3-diene was added thereto in small portions over 4 hours. After the addition was over, the mixture was left under stirring for 1 additional hour, whereupon it was hydrolyzed with an aqueous sodium carbonate solution. The excess of toluene was removed by means of a rotary evaporator under reduced pressure and the residue was distilled to give 101.7 g of the desired product having b.p. 70°-80°/26.6 Pa. A spectroscopic analysis indicated that the product obtained consisted of about 90% of isomer cis (a) and about 10% of trans (b).

Workup

  1. customequipped with a thermometer and a stirrer
  2. temperatureThe mixture was cooled to 10°
  3. additionAfter the addition
  4. waitwas left
  5. customThe excess of toluene was removed by means of a rotary evaporator under reduced pressure
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-5e3194a438384e5c82f6cc7df740eb27
Source dataset
uspto-grants-1987_06
Patent number
US04671798

Reaction notes

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