Methanol → Methyl 2-methyl-2-(4-methylphenyl)propanoate

HRID 1282115Notes

Reaction equation

HRID 1282115 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:19]O>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([O:11][CH3:19])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 123690852-Methyl-2-(4-methylphenyl)propanoic acid

Product 1

HCID 13296592Methyl 2-methyl-2-(4-methylphenyl)propanoate

Procedure

A solution of 2-(4-methylphenyl)-2-methylpropionic acid (60.0 g), sulfuric acid (0.6 ml) and methanol (300 ml) was refluxed for 19 hr. The solvent was evaporated, and water (200 ml) was added and the mixture was extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound (61.52 g) as a pale-brown oil. 1H-NMR(CDCl3)δ:1.56(6H, s), 2.32(3H, s), 3.64(3H, s), 7.13(2H, d, J=8.6 Hz), 7.22(2H, d, J=8.6 Hz). MS(EI): 192(M+).

Workup

  1. customThe solvent was evaporated
  2. additionwater (200 ml) was added
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-73b971b0f78a4a08b98222bbee99e8b4
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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