Catechol → HCID 5314503, compound

HRID 1917014Notes

Reaction equation

HRID 1917014 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].CO.C[O-].[Na+].Br[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>Cl>[CH:16]1([CH2:15][O:2][C:1]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 289CatecholHCID 887MethanolHCID 137636Cyclohexane, (bromomethyl)-HCID 10942334Sodium Methoxide

Product 1

HCID 5314503HCID 5314503, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

An oven-dried 10 mL round-bottom flask equipped with condenser was charged with catechol (198 mg, 1.80 mmol), MeOH (2 mL), and NaOMe (102 mg, 1.89 mmol) and purged with nitrogen. (Bromomethyl)cyclohexane (319 mg, 1.80 mmol) was added and the reaction was heated to reflux for 48 hours. After cooling to room temperature the reaction was diluted with 50 mL 1M HCl and extracted with DCM (3×25 mL). The combined organic layers were washed with saturated NaCl (1×25 mL), dried over sodium sulfate, and concentrated in vacuo. Purification by flash chromatography (3:1 hexane:Ethyl acetate) afforded an off-white solid weighing 114 mg (31% yield). Off-white solid; 1H NMR (CDCl3): δ 1.03-1.11 (m, 2H), 1.18-1.35 (m, 3H), 1.71-1.88 (m, 6H), 3.84 (d, J=6.35 Hz, 2H), 5.64 (s, 1H), 6.80-6.88 (m, 3H), 6.92-6.94 (m, 1H); 13C NMR (CDCl3): δ 25.88, 26.59, 30.05, 37.80, 74.39, 111.77, 114.55, 120.20, 121.14, 121.38, 145.99; HRMS (FAB): 206.13068 calcd for C13H18O2 [M]+. found 206.12952 (−5.7 ppm, −1.2 mmu).

Workup

  1. customAn oven-dried 10 mL round-bottom flask equipped with condenser
  2. custompurged with nitrogen
  3. temperaturethe reaction was heated
  4. temperatureto reflux for 48 hours
  5. extractionextracted with DCM (3×25 mL)
  6. washThe combined organic layers were washed with saturated NaCl (1×25 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography (3:1 hexane:Ethyl acetate)
  10. customafforded an off-white solid

Sources & evidence

ORD record
ord-979055adbee74a759e5fc7ab4bef3947
Source dataset
uspto-grants-2013_12
Patent number
US08618162B2

Reaction notes

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