Sulfuric Acid → tert-Butyl 3-methoxy-4-methylbenzoate

HRID 330149Notes

Reaction equation

HRID 330149 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([OH:8])=[O:7].S(=O)(=O)(O)O.[CH3:18][C:19](=[CH2:21])[CH3:20].[OH-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([O:8][C:19]([CH3:21])([CH3:20])[CH3:18])=[O:7]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255Isobutylene2×HCID 14798Sodium HydroxideHCID 815794-Methyl-m-anisic acid

Product 1

HCID 14708755tert-Butyl 3-methoxy-4-methylbenzoateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methoxy-4-methylbenzoic acid (10.0 g), concentrated sulfuric acid (1 ml), and condensed isobutylene (200 ml) in methylene chloride (200 ml) was placed in a pressure vessel and stirred for 16 hours. The vessel was then opened to vent unreacted isobutylene. The remaining liquid was poured into 10% (w/v) sodium hydroxide solution (150 ml) and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), and evaporated. The residue was purified by flash chromatography, eluting with 1:9 ethyl acetate:hexane, to give t-butyl 3-methoxy-4-methylbenzoate (9.1 g, 70%) as a colorless oil; NMR (80 MHz, CDCl3): 1.6[s, 9H, C(CH3)3 ], 2.27(s, 3H, CH3), 3.86(s, 3H, OCH3), 7.11(d, 1H), 7.49(m, 2H).

Workup

  1. customwas placed in a pressure vessel
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 1:9 ethyl acetate

Sources & evidence

ORD record
ord-f986eb038d204e0f9711c6a0830ef8e5
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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