Methanol → Methyl 4-(1-methylethoxy)benzoate

HRID 1695233

Reaction equation

HRID 1695233 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 729724-Isopropoxybenzoic acid

Product 1

HCID 3015807Methyl 4-(1-methylethoxy)benzoateYield 67%

Procedure

3.0 g of 4-isopropoxy-benzoic acid (16.7 mmol, 1.0 eq) were dissolved in MeOH (20 mL) and a catalytic quantity of sulfuric acid was added; the mixture was heated at reflux for 2 days. The solvent was then evaporated and the residue was dissolved in DCM and washed with 10% NaOH. The organic phases were dried and evaporated to give 2.2 g of title product (yield 67%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 days
  3. customThe solvent was then evaporated
  4. dissolutionthe residue was dissolved in DCM
  5. washwashed with 10% NaOH
  6. customThe organic phases were dried
  7. customevaporated

Sources & evidence

ORD record
ord-88acc85fdf57428c9d42bff593e1e905
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Linked notes

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