Diethyl Ether → HCID 19373458, compound

HRID 256629

Reaction equation

HRID 256629 reaction equation
[H-].[Na+].[C:3]([C:8]1[CH:13]=[C:12]([C:14]([CH2:17][CH3:18])([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=1[OH:19])([CH2:6][CH3:7])([CH3:5])[CH3:4].Br[C:21]1[CH:30]=[CH:29][C:28](OC)=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].CCCCCCC.[CH2:40]([O:42][CH2:43]C)C>N1C=CC=CC=1.[Cu]Cl.C(OCC)(=O)C>[C:3]([C:8]1[CH:13]=[C:12]([C:14]([CH2:17][CH3:18])([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=1[O:19][C:21]1[CH:30]=[CH:29][C:28]([CH2:40][O:42][CH3:43])=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])([CH2:6][CH3:7])([CH3:5])[CH3:4]

Participants

9

Reactant 5

HCID 3283Diethyl EtherHCID 84552,4-Di-tert-pentylphenolHCID 8900HeptaneHCID 24758Sodium hydrideHCID 2776849Methyl 2-bromo-5-methoxybenzoate

Product 1

HCID 19373458HCID 19373458, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 1049PyridineSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium hydride (1.2 g, 0.05 mol) in pyridine (60 mL), was added a solution of 2,4-di-tert-pentylphenol (12.9 g, 0.055 mol) in pyridine (20 mL) with stirring. Gas evolution ceased in approximately 1.5 hr at which time methyl 2-bromo-5-methoxylbenzoate was added. Copper (I) chloride (1.24 g, 0.0126 mol) was added and the mixture heated to reflux for 8 hours. The reaction mixture was diluted with diethyl ether (100 mL) and washed with 3N HCl (3×50 mL) and then washed with saturated sodium bicarbonate (1×50 mL). The organic extracts were dried over sodium sulfate, filtered and concentrated to give a dark oil. Chromatography on silica gel with 1:1 heptane:ethyl acetate yielded the pure product as a viscous oil in 90% yield. NMR and mass spectral analysis were consistent with proposed structure.

Workup

  1. additionwas added
  2. temperaturethe mixture heated
  3. temperatureto reflux for 8 hours
  4. washwashed with 3N HCl (3×50 mL)
  5. washwashed with saturated sodium bicarbonate (1×50 mL)
  6. dry with materialThe organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a dark oil

Sources & evidence

ORD record
ord-26886d3d31674d648fabaee48036271f
Source dataset
uspto-grants-1993_11
Patent number
US05258407

Linked notes

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