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

HRID 1003853Notes

Reaction equation

HRID 1003853 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

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 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).

Workup

  1. customwas refluxed for 5 hours
  2. concentrationThe mixture was concentrated by half
  3. additiondiluted with H2O
  4. extractionextracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-01368955834243c8a88831912aa0f809
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

Loading…