Cyclohexene oxide → HCID 123341624, compound

HRID 1467146Notes

Reaction equation

HRID 1467146 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>[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

5

Reactant 3

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

Product 1

HCID 123341624HCID 123341624, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 evaporated 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. customevaporated under reduced pressure until a small amount of ethanol
  3. additionThe solution was diluted with DCM
  4. washsuccessively washed with 1N HCl and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (Eluent: 0-20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-94870b030e3b4d3a99c692146066d5ed
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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