Methanol → Methyl 4-bromo-alpha-hydroxybenzeneacetate

HRID 6330

Reaction equation

HRID 6330 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:13]O.S(=O)(=O)(O)O>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])[C:9]([O:11][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 97930p-Bromomandelic acid

Product 1

HCID 14571696Methyl 4-bromo-alpha-hydroxybenzeneacetateYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 20 g (87 mmol) of (±)-4-bromo-α-hydroxyphenylacetic acid, 200 ml of methanol and 2 ml of concentrated sulfuric acid was stirred for 3 hours at room temperature. To the mixture 50 ml of water was added. After the solution was extracted with ethyl acetate, the organic extract was washed with a saturated aqueous solution of sodium bicarbonate and then with water, and it was dried on anhydrous magnesium sulfate. After removing the solvent, the residue was purified by chromatography (elution with toluene:ethyl acetate (2:1)), and 19.5 g of (±)-methyl 4-bromo-α-hydroxyphenylacetate was obtained (yield: 92%).

Workup

  1. extractionAfter the solution was extracted with ethyl acetate
  2. extractionthe organic extract
  3. washwas washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialwith water, and it was dried on anhydrous magnesium sulfate
  5. customAfter removing the solvent
  6. customthe residue was purified by chromatography (elution with toluene:ethyl acetate (2:1))

Sources & evidence

ORD record
ord-844e9b86e04349d6a419372f67937301
Source dataset
uspto-grants-1993_09
Patent number
US05248610

Linked notes

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