Benzene → beta-DAMASCONE

HRID 1579799Notes

Reaction equation

HRID 1579799 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[C:10](=[O:14])/[CH:11]=[CH:12]\[CH3:13].C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1[C:10](=[O:14])/[CH:11]=[CH:12]/[CH3:13]

Participants

5

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 1616260beta-Damascone, (Z)-

Product 1

HCID 5374527beta-DAMASCONEYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under an atmosphere of nitrogen, a solution containing 1.16 g. of cis-2,6,6-trimethyl-1-crotonoyl-1-cyclohexene prepared according to Example 18, 12 ml. of dry benzene and 0.023 g. of p-toluensulfonic acid were stirred 48 hours at room temperature. The solution was diluted with ether, neutralised and washed as usual. The volatile components were removed in vacuo and distillation gave a 90 % yield of trans-2,6,6-trimethyl-1-crotonoyl-1-cyclohexene, b.p. 78°-80°/0.001 Torr, the constants of which were found identical with those of the compound described in Example 12.

Workup

  1. additionUnder an atmosphere of nitrogen, a solution containing 1.16 g
  2. washneutralised and washed as usual
  3. customThe volatile components were removed in vacuo and distillation

Sources & evidence

ORD record
ord-cc54b928685146e396c524483a9a4a4d
Source dataset
uspto-grants-1976_01
Patent number
US03931326

Reaction notes

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