Water → 3-(Benzyloxy)-5-methylphenol

HRID 1977960Notes

Reaction equation

HRID 1977960 reaction equation
O.[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C)C=O>[CH2:13]([O:5][C:4]1[CH:3]=[C:2]([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 109983793-(Benzyloxy)-5-methylphenolYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Orcinol monohydrate (7.10 g, 50 mmol) in N,N-dimethylformamide (20 mL) was added dropwise to a mixture of NaH (95%, 24 g, 100 mmol) in N,N-dimethylformamide (60 mL) and the mixture was stirred at room temperature for 20 min. Benzyl bromide (8.55 g, 50 mmol) in N,N-dimethylformamide (20 mL) was added dropwise to the mixture and stirred at room temperature for 2 hours. Water (100 mL) was added slowly to the reaction mixture. The reaction mixture was extracted with ethyl acetate (3×100 mL) and then the organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After the solvent was evaporated, the residue was purified by flash column chromatography (silica gel, 3:1 hexane:ethyl acetate) to give the title compound as a yellow oil (5.20 g, 48%). 1H-NMR (300 MHz, CDCl3) δ7.39 (m, 5H), 6.40 (s, 1H), 6.29 (t, J=5.3 Hz, 1H), ), 6.26 (s, 1H), 5.25 (s, 1H), 4.99 (s, 2H), 2.26 (s, 3H).

Workup

  1. stirringstirred at room temperature for 2 hours
  2. extractionThe reaction mixture was extracted with ethyl acetate (3×100 mL)
  3. washthe organic phase was washed with brine (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter the solvent was evaporated
  6. customthe residue was purified by flash column chromatography (silica gel, 3:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-1d1611d4ff4a45388db82e4967bc66fd
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

Loading…