4-Hydroxybenzoic Acid → 4-(1-Cyclohexenyloxy)benzoic acid

HRID 365051Notes

Reaction equation

HRID 365051 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[C:13]1(Br)[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1.C(OCC)(=O)C>C1COCC1>[C:13]1([O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 5197751-Bromocyclohex-1-ene

Product 1

HCID 125732694-(1-Cyclohexenyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of p-hydroxybenzoic acid (1.38 gm, 10 mmol) in THF (30 ml) is added sodium hydride (0.48 g, 20 mmol), followed by cyclohexenyl bromide (1.63 gm 10 mM). The mixture is heated to reflux for 12 hours. After cooling the reaction mixture is poured into ethyl acetate and extracted with 1N NaOH (3×). The combined aqueous extracts are combined, acidified to pH 2 with concentrated HCl, and extracted 3× with ethyl acetate. The combined organic extracts are dried over Na2SO4 and evaporated under reduced pressure to afford the product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 12 hours
  3. temperatureAfter cooling the reaction mixture
  4. extractionextracted with 1N NaOH (3×)
  5. extractionextracted 3× with ethyl acetate
  6. dry with materialThe combined organic extracts are dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customto afford the product

Sources & evidence

ORD record
ord-20c96d6f10544cb7842b6e09d05999a5
Source dataset
uspto-grants-1986_08
Patent number
US04607053

Reaction notes

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