Dimethylformamide → Methyl 4-hydroxy-3-methylbenzoate

HRID 713032Notes

Reaction equation

HRID 713032 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].[CH3:12]N(C=O)C.S(Cl)(Cl)=O>CO>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 681384-Hydroxy-3-methylbenzoic acid

Product 1

HCID 11240684Methyl 4-hydroxy-3-methylbenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-hydroxy-3-methylbenzoic acid (10.00 g, 65.7 mmol) and DMF (100 μL) in MeOH (35 mL) was added dropwise thionyl chloride (4.8 mL, 65.7 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with the addition of aqueous saturated sodium bicarbonate solution (50 mL), and methanol was removed under reduced pressure. The residue was extracted with EtOAc (3×50 mL) and dried over sodium sulfate, filtered and concentrated in vacuo to provide methyl 4-hydroxy-3-methyl-benzoate (10.53 g, 96%) as a light brown solid. ESI-MS m/z calc. 166.0. found 167.1 (M+1)+; Retention time: 1.09 minutes (3 min run).

Workup

  1. customThe reaction mixture was quenched with the addition of aqueous saturated sodium bicarbonate solution (50 mL), and methanol
  2. customwas removed under reduced pressure
  3. extractionThe residue was extracted with EtOAc (3×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-376a5128df794a1aad6427df1bf7208f
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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