Benzyl Bromide → Methyl 3-(benzyloxy)-5-hydroxy-4-methylbenzoate

HRID 1688305Notes

Reaction equation

HRID 1688305 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:13])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:13])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11458051Methyl 3,5-dihydroxy-4-methylbenzoate

Product 1

HCID 67211670Methyl 3-(benzyloxy)-5-hydroxy-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3,5-dihydroxy-4-methylbenzoate (3.5 g, 19.22 mmol, 1.0 eq) was dissolved in 300 ml of DMF. To this solution potassium carbonate (2.52 g, 18.26 mmol, 0.95 eq) was added. To this stirred suspension, benzyl bromide (3.12 g, 18.26 mmol, 0.95 eq) (diluted with 50 ml of DMF) was added dropwise over a period of 3 h. The solution was stirred overnight at ambient temperature. Then DMF was evaporated under reduced pressure. The residue was washed with water and the product was extracted thrice with DCM. The combined DCM layers was dried over sodium sulphate and evaporated under vacuum. The required product was purified by silica gel (240-400) column chromatography using 10% ethyl acetate/hexane as the eluent. Yield: 1.6 g (30%). 1H NMR (400 MHz, DMSO-d6): δ 2.07 (s, 3H), 3.81 (s, 3H), 5.14 (s, 2H), 7.08 (s, 1H), 7.14 (s, 1H), 7.33-7.35 (d, 1H, J=7.04 Hz), 7.39-7.42 (t, 2H, J=7.40 Hz), 7.46-7.48 (d, 2H, J=7.48 Hz), 9.78 (s, 1H).

Workup

  1. customThen DMF was evaporated under reduced pressure
  2. washThe residue was washed with water
  3. extractionthe product was extracted thrice with DCM
  4. dry with materialThe combined DCM layers was dried over sodium sulphate
  5. customevaporated under vacuum
  6. customThe required product was purified by silica gel (240-400) column chromatography

Sources & evidence

ORD record
ord-1bf21d893d054dd58428b914d035f980
Source dataset
uspto-grants-2012_04
Patent number
US08148382B2

Reaction notes

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