Methanol → Methyl 3-tert-butyl-5-hydroxybenzoate

HRID 658012Notes

Reaction equation

HRID 658012 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([OH:14])[CH:13]=1)[C:8]([OH:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[CH3:19]O>>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([OH:14])[CH:13]=1)[C:8]([O:10][CH3:19])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 217986673-t-Butyl-5-hydroxybenzoic acid

Product 1

HCID 53399216Methyl 3-tert-butyl-5-hydroxybenzoate

Procedure

3-tert-Butyl-5-hydroxybenzoic acid (O7.043; 1.93 g) was dissolved in methanol (20 ml), and thionyl chloride (0.937 ml) was slowly added dropwise while stirring. After stirring at 65° C. for 1 h, the mixture was dried, the residue was taken up in DCM, and the solution was washed with saturated sodium hydrogencarbonate solution, dried over MgSO4, filtered and concentrated by rotary evaporation. 2.19 g of the title compound were obtained.

Workup

  1. stirringAfter stirring at 65° C. for 1 h
  2. customthe mixture was dried
  3. washthe solution was washed with saturated sodium hydrogencarbonate solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-8f7918bb922e41f69af01e0981c90031
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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