Methanol → HCID 54376030, compound

HRID 1585463Notes

Reaction equation

HRID 1585463 reaction equation
C[O:2][C:3]1[C:4]([CH3:14])=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[S:7].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[C:4]([CH3:14])=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[S:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 54217787HCID 54217787, compound

Product 1

HCID 54376030HCID 54376030, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10 g (0.044 mol) of methyl 3-methoxy-2-methyl-4-methylthiobenzoate was dissloved in 90 ml of methylene chloride, and the solution was added dropwise to 90 ml of methylene chloride containing 8.4 ml (0.088 mol) of boron tribromide at 5 to 10° C. After stirring at room temperature for 4 hours, 50 ml of methanol was added dropwise under ice cooling, and the solution was then washed with water and next a saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 9.2 g of methyl 3-hydroxy-2-methyl-4-methylthiobenzoate. Yield=98%.

Workup

  1. washthe solution was then washed with water and next a saturated sodium chloride solution
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-82c2d973f58541229c898e5ce3141e02
Source dataset
uspto-grants-1999_08
Patent number
US05939360

Reaction notes

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