Sulfuric Acid → HCID 19867563, compound

HRID 1198962Notes

Reaction equation

HRID 1198962 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+].[CH2:24](Cl)Cl>>[CH2:1]([O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([O:8][C:19]([CH3:20])([CH3:18])[CH3:21])=[O:7])[CH3:24]

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 8255Isobutylene2×HCID 14798Sodium HydroxideHCID 815794-Methyl-m-anisic acid

Product 1

HCID 19867563HCID 19867563, compoundYield 70%

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 on silica gel (700 ml), eluting with 1:9 ethyl acetate:hexane, to give t-butyl 3-ethoxy-4methylbenzoate (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 on silica gel (700 ml)
  7. washeluting with 1:9 ethyl acetate

Sources & evidence

ORD record
ord-4d20daf50ea04a1297b3cfb593a1ce0b
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

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