Oxygen → Methyl cyclohex-1-ene-1-carboxylate

HRID 1413223Notes

Reaction equation

HRID 1413223 reaction equation
C1(C(O)C(Cl)(Cl)Cl)CCCC=C1.O=O.[Na].[CH:16]1([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]1>CO.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[C:16]1([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=1

Participants

7

Reactant 4

HCID 977OxygenHCID 5360545SodiumHCID 11007985Methyl cyclohex-2-ene-1-carboxylateHCID 12418397HCID 12418397, compound

Product 1

HCID 87647Methyl cyclohex-1-ene-1-carboxylateYield 59%

Reagents, catalysts & solvents 2

HCID 212261,10-Phenanthroline hydrateCatalyst2×HCID 887MethanolSolvent3×

Procedure

1-(2-Cyclohexen-1-yl)-2,2,2-trichloroethanol (20 g; 87.3 m. moles) was added to a solution of cupric chloride dihydrate (0.25 g; 1.47 m. moles) and a 1,10-phenanthroline hydrate (0.75 g; 3.8 m. moles) in methanol (150 ml). A rapid stream of oxygen was passed through the vigorously stirred solution and a solution of sodium (2.5 g; 108.5 m. moles) in methanol (50 ml) was added over a period of 41/4 hours. A solution of cupric chloride dihydrate (0.125 g; 0.733 m. moles) and 1,10-phenanthroline hydrate (0.375 g; 1.9 m. moles) in methanol (10 ml) was then added and the reaction allowed to proceed for a further 11/4 hours at a temperature of 20°-25° C. The reaction mixture was poured into ice-cold dilute hydrochloric acid, extracted with ether (4×100 ml) and the combined extracts washed twice with dilute aqueous sodium carbonate. The dried (MgSO4) extract was evaporated and the residue distilled to give a mixture of methyl 2-cyclohexene-1-carboxylate and methyl 1-cyclohexene-1-carboxylate (7.2 g; yield 59%), b.p. 80°-85° C./12 mm, containing about 90% of the former as indicated by G.L.C.

Workup

  1. custom4 hours
  2. customat a temperature of 20°-25° C
  3. additionThe reaction mixture was poured into ice-cold dilute hydrochloric acid
  4. extractionextracted with ether (4×100 ml)
  5. washthe combined extracts washed twice with dilute aqueous sodium carbonate
  6. dry with materialThe dried (MgSO4)
  7. extractionextract
  8. customwas evaporated
  9. distillationthe residue distilled
  10. customto give

Sources & evidence

ORD record
ord-458a6342f00d405ca12bfc5fd7bcc3d7
Source dataset
uspto-grants-1981_02
Patent number
US04249015

Reaction notes

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