Sodium Bicarbonate → Methyl 2-hydroxy-6-methoxymethylbenzoate

HRID 59675Notes

Reaction equation

HRID 59675 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][Si](C(C)(C)C)(C)C)[C:4]=1[C:5]([O:7][CH3:8])=[O:6].[C:21](=O)(O)[O-:22].[Na+]>CO>[OH:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:3]([CH2:2][O:22][CH3:21])[C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 25170261Methyl 2-bromomethyl-6-(tert-butyldimethylsilyloxy)benzoate2×

Product 1

HCID 89704969Methyl 2-hydroxy-6-methoxymethylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-bromomethyl-6-(tert-butyldimethylsilyloxy)benzoate (Intermediate 12, 4.26 g) in methanol (63 mL) was stirred and heated at reflux overnight. After cooling, the mixture was basified by addition of solid sodium bicarbonate and then evaporated to dryness. The residue was triturated with DCM and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25% to give methyl 2-hydroxy-6-methoxymethylbenzoate (1.46 g) as a white crystalline solid.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. customevaporated to dryness
  5. customThe residue was triturated with DCM
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25%

Sources & evidence

ORD record
ord-a27c6335f7d34fb3be4947c9a70e0309
Source dataset
uspto-grants-2016_09
Patent number
US09440943B2

Reaction notes

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