Acetylresorcinol → 3-Benzyloxyphenyl acetate

HRID 651533

Reaction equation

HRID 651533 reaction equation
[C:1]([O:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[C:1]([O:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([O:8][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5055AcetylresorcinolHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 223458653-Benzyloxyphenyl acetateYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Resorcinol monoacetate (6.10 g, 40 mmol) in DMF (10 mL) was added dropwise to the mixture of NaH (95%, 0.92 g, 40 mmol) in DMF (50 mL). The mixture was stirred at room temperature for 10 min. Benzyl bromide (6.85 g, 40 mmol) in DMF (10 mL) was then added dropwise, and the mixture was stirred at room temperature for 2 h. The reaction mixture was quenched slowly with water (100 mL) and then extracted with ethyl acetate (3×100 mL). The organic phase was washed with brine (2×50 mL) and dried over Na2SO4. The solvent was removed in vacuo and the residue purified by flash column chromatography (1:1 hexane:methylene chloride) to give the title compound as a white solid (5.30 g, 55%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. customThe reaction mixture was quenched slowly with water (100 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe organic phase was washed with brine (2×50 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by flash column chromatography (1:1 hexane:methylene chloride)

Sources & evidence

ORD record
ord-22dae3b01e214b0f815d70d11b962c65
Source dataset
uspto-grants-2001_08
Patent number
US06281206B1

Linked notes

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