Sodium Bicarbonate → Methyl 3-methoxymethyl-4-hydroxy-5-methylbenzoate

HRID 1641996Notes

Reaction equation

HRID 1641996 reaction equation
C([O:4][C:5]1[C:14]([CH3:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH2:16]Br)(=O)C.[C:18](=O)(O)[O-:19].[Na+]>CO>[CH3:18][O:19][CH2:16][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([CH3:15])[C:5]=1[OH:4])[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59283833Methyl 4-acetoxy-3-bromomethyl-5-methylbenzoate

Product 1

HCID 59283873Methyl 3-methoxymethyl-4-hydroxy-5-methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of crude methyl 4-acetoxy-3-bromomethyl-5-methylbenzoate (4.63 g, 0.00154 mol) in methanol (100 mL) was mixed with sodium bicarbonate (6.48 g, 5 equivalents). The mixture was refluxed under a nitrogen atmosphere. After 1.5 hours, TLC analysis showed complete conversion. The reaction was cooled to room temperature and evaporated to dryness. The residue was partitioned between ethyl acetate (100 mL) and water (100 mL). The ethyl acetate layer was separated and washed with water. It was then dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The crude product (1.5 g) was purified by flash chromatography on silica using 10% ethyl acetate/hexanes as eluent. Purified Yield=0.833 g (40%), white waxy solid.

Workup

  1. temperatureThe mixture was refluxed under a nitrogen atmosphere
  2. customevaporated to dryness
  3. customThe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. customThe ethyl acetate layer was separated
  5. washwashed with water
  6. dry with materialIt was then dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe crude product (1.5 g) was purified by flash chromatography on silica using 10% ethyl acetate/hexanes as eluent
  10. customPurified Yield=0.833 g (40%), white waxy solid

Sources & evidence

ORD record
ord-fb58dd7d89214216a6117b1c36da561d
Source dataset
uspto-grants-2012_02
Patent number
US08119422B2

Reaction notes

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