Sulfuric Acid → 4-(4-Chlorophenyl)-cyclohex-3-enecarboxylic acid

HRID 1939883Notes

Reaction equation

HRID 1939883 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][CH:11]([C:14]([O:16]CC)=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.OS(O)(=O)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21465094Ethyl 4-(4-chlorophenyl)-4-hydroxy-cyclohexanecarboxylate

Product 1

HCID 214650994-(4-Chlorophenyl)-cyclohex-3-enecarboxylic acidYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve the product (1.75 g) from STEP 1 in THF (100 mL), treat with 40% H2SO4 (25 mL) and heat the reaction mixture at reflux for 5.5 h. Remove most of the solvent in vacuo, dilute the reaction mixture with water and extract with Et2O. Separate the organic layer and concentrate to give 4-(4-chlorophenyl)-cyclohex-3-enecarboxylic acid (1.36 g).

Workup

  1. temperatureheat the reaction mixture
  2. temperatureat reflux for 5.5 h
  3. customRemove most of the solvent in vacuo
  4. additiondilute the reaction mixture with water
  5. extractionextract with Et2O
  6. customSeparate the organic layer
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-c2aa203d1a73445b97568eeac8d28110
Source dataset
uspto-grants-1997_12
Patent number
US05698548

Reaction notes

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