Hydrochloric Acid → Methyl cyclohex-1-ene-1-carboxylate

HRID 1413224Notes

Reaction equation

HRID 1413224 reaction equation
[CH:1]1([C:7]([O:9][CH3:10])=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[Na].Cl>CO>[C:1]1([C:7]([O:9][CH3:10])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 11007985Methyl cyclohex-2-ene-1-carboxylate

Product 1

HCID 87647Methyl cyclohex-1-ene-1-carboxylateYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-cyclohexene-1-carboxylate (4.0 g; 28.5 m. moles) was added to a solution of sodium (0.73 g; 31.7 m. moles) in methanol (20 ml) and the mixture was allowed to stand at room temperature for a period of 21/2 hours. The mixture was poured into dilute hydrochloric acid, extracted with ether (4×25 ml) and the combined extracts washed with dilute aqueous sodium carbonate and then water. The dried (MgSO4) extract was evaporated and the residue distilled to give methyl 1-cyclohexene-1-carboxylate (3.5 g; yield 87.5%), b.p. 84° C./15 mm.

Workup

  1. extractionextracted with ether (4×25 ml)
  2. washthe combined extracts washed with dilute aqueous sodium carbonate
  3. dry with materialThe dried (MgSO4)
  4. extractionextract
  5. customwas evaporated
  6. distillationthe residue distilled

Sources & evidence

ORD record
ord-aab44d68fe3b4b499e5282b93b4398db
Source dataset
uspto-grants-1981_02
Patent number
US04249015

Reaction notes

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