Cyclohexene oxide → HCID 123341624, compound

HRID 2047886Notes

Reaction equation

HRID 2047886 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[CH2:14]1[CH2:19][CH:18]2[O:20][CH:17]2[CH2:16][CH2:15]1.[C:21]([O-])([O-])=O.[K+].[K+]>C(O)C.C(Cl)Cl>[OH:20][CH:17]1[CH2:18][CH2:19][CH2:14][CH2:15][CH:16]1[O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH2:8][CH3:21])=[O:6]

Participants

6

Reactant 3

HCID 9246Cyclohexene oxideHCID 11430Potassium CarbonateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 123341624HCID 123341624, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-hydroxy-4-methoxybenzoate (210 mg, 1.15 mmol) and cyclohexane oxide (466 uL, 4.61 mmol) in ethanol (11 mL) was added K2CO3 (637 mg, 4.61 mmol) at room temperature. The reaction mixture was then refluxed overnight then cooled down to room temperature, and evapotreted under reduced pressure until a small amount of ethanol remained. The solution was diluted with DCM and successively washed with 1N HCl and brine, dried over Na2SO4 filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (Eluent: 0-20% EtOAc/Hexanes) to afford (±)-ethyl 3-((2-hydroxycyclohexyl)oxy)-4-methoxy-benzoate as a colorless oil (307 mg, 91%). 1H NMR (400 MHz, DMSO-d6) δ 1.16-1.34 (m, 7H), 1.61 (m, 2H), 1.84-1.94 (m, 2H), 3.55 (m, 1H), 3.83 (s, 3H), 4.03 (m, 1H), 4.28 (q, J=8.0 Hz, 2H), 4.85 (d, J=4.0 Hz, 1H), 7.05 (d, J=12.0 Hz, 1H), 7.55-7.58 (m, 2H).

Workup

  1. temperatureThe reaction mixture was then refluxed overnight
  2. washsuccessively washed with 1N HCl and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel (Eluent: 0-20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-85ac0fb12361433aaaba882b26f2eff9
Source dataset
uspto-grants-2013_11
Patent number
US08592592B2

Reaction notes

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