Water → 3-(Benzyloxy)-5-methylphenol

HRID 482086Notes

Reaction equation

HRID 482086 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=O)C>[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 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Orcinol monohydrate (7.10 g, 50 mmol) in DMF (20 mL) was added dropwise to NaH (95%, 2.4 g, 100 mmol) in DMF (60 mL). The reaction mixture was stirred at room temperature for 20 min. Benzyl bromide (8.55 g, 50 mmol) in DMF (20 mL was then added dropwise and the reaction mixture was stirred at room temperature for 2 h. Water (100 mL) was added slowly followed by extraction with ethyl acetate (3×100 mL). The organic phase was washed with brine (2×50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was then purified by flash column chromatography (3:1 hexane:ethyl acetate) to give the title compound as a yellow oil (3.15 g, 31%). 1H-NMR (300 MHz, CDCl3) 2.26 (s, 3H), 4.99 (s, 2H), 5.25 (s, 1H), 6.26 (s, 1H), 6.29 (t, 1H), 6.40 (s, 1H), 7.39 (m, 5H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. extractionfollowed by extraction with ethyl acetate (3×100 mL)
  3. washThe organic phase was washed with brine (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by flash column chromatography (3:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-694d560fdb1f4a758c5fa07a156fd5c4
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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