Water → 3-(Benzyloxy)-5-methylphenol

HRID 442902

Reaction equation

HRID 442902 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 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Orcinol monohydrate (7.10 g, 50 mmol) in N,N-dimethylformamide (20 mL) was added dropwise to NaH (2.4 g, 100 mmol) in N,N-dimethylformamide (60 mL). The reaction mixture was stirred at room temperature for 20 min. Benzyl bromide (8.55 g, 50 mmol) in N,N-dimethylformamide (20 mL) was then added, and the reaction mixture was stirred at ambient temperature for 2 hours. Water (100 mL) was added carefully followed by extraction by 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 purified by flash column chromatography (3:1 hexane/ethyl acetate) to give the title compound as a yellow oil (3.40 g, 32%). 1H-NMR (300 MHz, CDCl3) δ 7.39 (m, 5 H), 6.40 (s, 1 H), 6.29 (s, 1 H), 6.26 (s, 1 H), 5.00 (s, 2 H), 4.89 (s, 1 H), 2.26 (s, 3 H).

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 2 hours
  2. extractionfollowed by extraction by 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 purified by flash column chromatography (3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-67ceae663c734f78b75f5827032301ed
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Linked notes

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