Methanol → Methyl 5-(tert-butyl)-4-hydroxy-2-methylbenzoate

Reaction equation

[C:1]([C:5]1[C:6]([O:15]COCCOC)=[CH:7][C:8]([CH3:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2].OS(O)(=O)=O.[CH3:27]O>>[CH3:27][O:12][C:10](=[O:11])[C:9]1[CH:13]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:15])=[CH:7][C:8]=1[CH3:14]

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 540668455-tert-Butyl-4-(2-methoxy-ethoxymethoxy)-2-methyl benzoic acid

Product 1

HCID 10632819Methyl 5-(tert-butyl)-4-hydroxy-2-methylbenzoate

Procedure

A solution of 5-tert-butyl-4-(2-methoxy-ethoxymethoxy)-2-methyl benzoic acid from Example AAA (20.9 g, 70.5 mmol), MeOH (150 mL), and H2SO4 (10 mL) was refluxed for 5 hours and stirred overnight at room temperature. The mixture was concentrated by half, diluted with H2O, and extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4), and concentrated to give the title compound. 1H NMR (CDCl3) δ 1.36 (s, 9 H), 2.48 (s, 3 H), 3.82 (s, 3 H), 6.48 (s, 1 H), 7.87 (s, 1 H).