Methyl iodide → HCID 89580785, compound

HRID 1501087Notes

Reaction equation

HRID 1501087 reaction equation
[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][CH:4]=1.[H-].[Na+].I[CH3:25]>CN(C)C=O>[CH3:25][O:1][CH:2]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11437583HCID 11437583, compound

Product 1

HCID 89580785HCID 89580785, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 4-(hydroxy(phenyl)methyl)benzoate (1.4 g, 4.9 mmol) was dropped to the suspension of sodium hydride (237 mg, 5.9 mmol) in N,N-dimethylformamide (20 mL) and then the mixture was stirred 0.5 hour. Then iodomethane (3.0 mL) was added to the mixture and stirred at room temperature for 2 hours. The resultant mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1) to give tert-butyl 4-(methoxy(phenyl)methyl)benzoate as a colorless oil (1.25 g, 86%). 1H NMR (300 MHz, CDCl3): δ 7.95 (d, J=8.1 Hz, 2H), 7.42-7.31 (m, 7H), 5.28 (s, 1H), 3.39 (s, 3H), 1.58 (s, 9H).

Workup

  1. stirringstirred at room temperature for 2 hours
  2. concentrationThe resultant mixture was concentrated
  3. customto give a residue
  4. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1)

Sources & evidence

ORD record
ord-7e583185a1b54934b57135b3be0c3277
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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