Hydrochloric Acid → 1-Cyclohexene-1-carboxylic acid, ethyl ester

HRID 1413225Notes

Reaction equation

HRID 1413225 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.[CH2:13](O)C>>[C:1]1([C:7]([O:9][CH2:10][CH3:13])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5360545SodiumHCID 11007985Methyl cyclohex-2-ene-1-carboxylate

Product 1

HCID 741731-Cyclohexene-1-carboxylic acid, ethyl esterYield 90%

Procedure

Methyl 2-cyclohexene-1-carboxylate (5.6 g; 40 m. moles) was added to a solution of sodium (1.1 g; 47.8 m. moles) in ethanol (35 ml) and the mixture was allowed to stand at room temperature for a period of 11/2 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. The dried (MgSO4) extract was evaporated and the residue distilled to give ethyl 1-cyclohexene-1-carboxylate (5.5 g; yield 90%), b.p. 92° C./15 mm (N.M.R.: 6.7-7.0 (m,1,CH=C), 3.9-4.25 (q,2,CH2CH3), 1.95-2.42 (m,4,allylic CH2), 1.13-1.42 (t,3,CH2CH3) 1.45-1.92 (m,4,CH2 --CH2)).

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-6cfda5e2eb664e7393d4442e536c3eb3
Source dataset
uspto-grants-1981_02
Patent number
US04249015

Reaction notes

Loading…