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

HRID 356497Notes

Reaction equation

HRID 356497 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].[CH3:22]O>>[CH3:22][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

3

Reactant 2

HCID 887MethanolHCID 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 H2 SO4 (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-0d36a1b7f1744ed29db2081aac03dc59
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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