Thionyl Chloride → Methyl 4-hydroxy-3-methylbenzoate

HRID 1641997Notes

Reaction equation

HRID 1641997 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].S(Cl)(Cl)=O.[C:16](=O)(O)[O-].[Na+]>CO>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 681384-Hydroxy-3-methylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 11240684Methyl 4-hydroxy-3-methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-hydroxy-3-methylbenzoic acid (Matrix Scientific, 1 g) was dissolved in methanol and cooled in an ice-bath under a nitrogen atmosphere. Thionyl chloride (5 mL) was added slowly. The reaction was stirred at 0° C. for one hour and then warmed to room temperature and stirred for 16 hours. Solid sodium bicarbonate was then added to neutralize the acid and the mixture was evaporated to dryness. The residue was partitioned between ethyl acetate (75 mL and water (100 mL). The ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to afford 1.0 g of product.

Workup

  1. temperaturecooled in an ice-bath under a nitrogen atmosphere
  2. temperaturewarmed to room temperature
  3. stirringstirred for 16 hours
  4. customthe mixture was evaporated to dryness
  5. customThe residue was partitioned between ethyl acetate (75 mL and water (100 mL)
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-af07b786fdc54040a1adcae62e39952e
Source dataset
uspto-grants-2012_02
Patent number
US08119422B2

Reaction notes

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