Dimethylformamide → Methyl 4-hydroxy-3-methylbenzoate

HRID 713020Notes

Reaction equation

HRID 713020 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 (10.0 g, 65.7 mmol) and DMF (100 μL) in methanol (35 mL) was added dropwise thionyl chloride (7.8 g, 4.8 mL, 65.7 mmol). The reaction mixture was allowed to stir 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 in vacuo. The aqueous layer was then extracted with EtOAc (3×50 mL). The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide methyl 4-hydroxy-3-methyl-benzoate (10.5 g, 96%) as a light brown solid. ESI-MS m/z calc. 166.4. found 167.4 (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 in vacuo
  3. extractionThe aqueous layer was then extracted with EtOAc (3×50 mL)
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d75309d2d7c140cc94494b0a743253dd
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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