Methanol → Methyl 5-hydroxy-2-methylbenzoate

HRID 1914250Notes

Reaction equation

HRID 1914250 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:12])=[O:8]

Participants

3

Reactant 2

HCID 887MethanolHCID 2351885-Hydroxy-2-methylbenzoic acid

Product 1

HCID 13929055Methyl 5-hydroxy-2-methylbenzoate

Procedure

To a mixture of 107 g 5-hydroxy-2-methylbenzoic acid (compound described in example F1 step 2) in 1000 ml methanol 251.1 g thionylchloride is added dropwise. The mixture is heated to reflux and stirred two hours at RT. After the solvent has been largely evaporated from the mixture under reduced pressure, 100 ml water are added and the reaction mixture is adjusted to pH 7 with saturated aqueous sodium hydrogen carbonate solution. The aqueous phase is extracted with 200 ml EA three times, the combined organics are dried over MgSO4, and the solvent is removed under reduced pressure yielding methyl 5-hydroxy-2-methylbenzoate, which is used for the next step without further purification.

Workup

  1. additionis added dropwise
  2. temperatureThe mixture is heated
  3. temperatureto reflux
  4. customAfter the solvent has been largely evaporated from the mixture under reduced pressure, 100 ml water
  5. additionare added
  6. extractionThe aqueous phase is extracted with 200 ml EA three times
  7. dry with materialthe combined organics are dried over MgSO4
  8. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-7783914f8b2a4db1bb4ca8feb1234f01
Source dataset
uspto-grants-2013_12
Patent number
US08609848B2

Reaction notes

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