Methanol → Methyl 4-(1,1-dimethylethyl)-3-methoxybenzoate

HRID 1158463Notes

Reaction equation

HRID 1158463 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].OS(O)(=O)=O.[CH3:21]O>O>[CH3:21][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[C:6]([O:14][CH3:15])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 127397584-tert-Butyl-3-methoxybenzoic acid

Product 1

HCID 68616936Methyl 4-(1,1-dimethylethyl)-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-tert-butyl-3-methoxy-benzoic acid (3.00 g, 14.4 mmol; commercially available from Apin, 41226B) in MeOH (30 mL) is added H2SO4 conc. (3 mL) and the mixture is refluxed for 5 hrs. After cooling, the mixture is diluted with water, extracted twice with diethyl ether, the combined organics are dried (Na2SO4) and evaporated to dryness to give the title compound as yellowish oil. MS: 223.0 [M+H]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 6.12 min. 1H-NMR (CDCl3): δ 1.41 (s, 9H), 3.91 (s, 3H), 3.92 (s, 3H), 7.36 (dd, 1H), 7.54 (d, 1H), 7.60 (dd, 1H) ppm.

Workup

  1. temperaturethe mixture is refluxed for 5 hrs
  2. temperatureAfter cooling
  3. extractionextracted twice with diethyl ether
  4. dry with materialthe combined organics are dried (Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-d08a89f71cd84b409999c5fb89fe91c9
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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