Sulfuric Acid → 1-(3-tert-Butoxyphenyl)ethan-1-one

HRID 441177Notes

Reaction equation

HRID 441177 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:11][C:12](=[CH2:14])[CH3:13].OS(O)(=O)=O>ClCCl>[C:12]([O:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1)([CH3:14])([CH3:13])[CH3:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 84873-Hydroxyacetophenone

Product 1

HCID 135462911-(3-tert-Butoxyphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3'-hydroxyacetophenone (22.64 g), isobutylene (300 mL) and concentrated H2SO4 (1 mL) in dry dichloromethane (310 mL) was stirred in a sealed pressure vessel at room temperature for 3 days. After the reaction vessel was vented, the organic phase was washed (10% NaOH, water and brine), dried and evaporated to an oil (25.95 g) which was purified by chromatography, eluting with dichloromethane:ethyl acetate, to give 3'-tert-butoxyacetophenone (22.62 g); TLC: Rf =0.55, ethyl acetate:dichloromethane (3:97); MS: m/z=193(M+1).

Workup

  1. washthe organic phase was washed (10% NaOH, water and brine)
  2. customdried
  3. customevaporated to an oil (25.95 g) which
  4. customwas purified by chromatography
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-b2fda2dafd5646c785dadc253ef0ea92
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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