Hydrochloric Acid → Methyl 4-hydroxy-3-methylbenzoate

HRID 393290Notes

Reaction equation

HRID 393290 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].Cl.[CH3:13]O>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:13])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 681384-Hydroxy-3-methylbenzoic acid

Product 1

HCID 11240684Methyl 4-hydroxy-3-methylbenzoateYield 84%

Procedure

A solution of 4-hydroxy-3-methylbenzoic acid (5.13 g, 33.7 mmol) and aqueous 12 N HCl solution (1.0 mL) in MeOH (100 mL) was heated to reflux for 16 h. The cooled reaction mixture was concentrated under reduced pressure and the residue was taken in EtOAc. The resulting solution was washed with aqueous saturated NaHCO3 solution and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was triturated with Hexane:EtOAc (9:1) to give the title compound (4.70 g, 84% yield) as a beige solid.

Workup

  1. temperatureto reflux for 16 h
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. washThe resulting solution was washed with aqueous saturated NaHCO3 solution and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with Hexane:EtOAc (9:1)

Sources & evidence

ORD record
ord-9829a15de80f4c48b520881201dc150c
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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