6-Methylcyclohex-3-ene-1-carboxylic acid → HCID 11208673, compound

HRID 842436Notes

Reaction equation

HRID 842436 reaction equation
CC1C(C(OC(C)(C)C)=O)CCC(Cl)C1.[CH3:16][CH2:17][O:18][C:19]([CH:21]1[CH:26]([CH3:27])[CH2:25][CH2:24][CH:23]([I:28])[CH2:22]1)=[O:20].C[C@H]1[C@H](C(O)=O)CC=CC1.CC1C(C(O)=O)CC=CC1>>[I:28][C@H:23]1[CH2:22][C@@H:21]([C:19]([O:18][CH2:17][CH3:16])=[O:20])[C@H:26]([CH3:27])[CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 2212786-Methylcyclohex-3-ene-1-carboxylic acidHCID 546164tert-Butyl 4-chloro-2-methylcyclohexane carboxylateHCID 113095553-Cyclohexene-1-carboxylic acid, 6-methyl-, (1R,6R)-rel-HCID 14833761HCID 14833761, compound

Product 1

HCID 11208673HCID 11208673, compoundYield 15%

Procedure

Test compounds: Liquid trimedlure (UOP Chemicals, East Rutherford, N.J.) (98% pure; density 1.02 g/ml) and ceralure (Agrisense/Biosys, Palo Alto, Calif.) (98% pure; density 1.43 g.ml) were purchased from commercial sources. The 2 g polymeric plug (Agrisense/Biosys, Palo Alto, Calif.) was the same product used by action agencies such as USDA-APHIS and California Department of Food and Agriculture (CDFA) in their surveillance and detection programs against medfly. The enantiomers of ceralure B1 (ethyl-cis-5-iodo-trans-2-methylcyclohexane-1-carboxylate) (henceforth referred to as the 1R,2R,5R and 1S,2S,5S enantiomers respectively) were synthesized using the 9 step process (described above) which yielded both enantiomers with high purity (97% ) and an overall yield of 15%. The racemic mixture of the two enantiomers was produced starting from racemic (5), which is (1RS, 6RS)-6-methyl-3-cyclohexene-1-carboxylic acid, using the above described process used to produce ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate (4a).

Workup

  1. customwere synthesized
  2. customyielded both enantiomers with high purity (97% )
  3. additionThe racemic mixture of the two enantiomers
  4. customwas produced

Sources & evidence

ORD record
ord-820e86561ce14ee79a52959fbcf83850
Source dataset
uspto-grants-2002_04
Patent number
US06375943B1

Reaction notes

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