3-Hydroxy-2-methylbenzoic Acid → Ethyl 3-hydroxy-2-methylbenzoate

HRID 1958855Notes

Reaction equation

HRID 1958855 reaction equation
[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].O.[C:13]1(C)C=CC(S(O)(=O)=O)=C[CH:14]=1>C(O)C>[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:13][CH3:14])=[O:6]

Participants

4

Reactant 2

HCID 2520233-Hydroxy-2-methylbenzoic AcidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 15376194Ethyl 3-hydroxy-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-Hydroxy-2-methylbenzoic acid (5.04 g, 33.12 mmol) and p-Toluenesulfonic acid monohydrate (0.741 g, 3.89 mmol) in abs ethanol (150 ml) was refluxed for 16 hours or until all the starting material is consumed. The reaction mixture was concentrated, diluted with EtOAc (30 ml) and washed with water (20 ml). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1) to give the title compound.

Workup

  1. customis consumed
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with EtOAc (30 ml)
  4. washwashed with water (20 ml)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-a1ed2547fa1441b6930316f653c25469
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

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