Sulfuric Acid → HCID 10634286, compound

HRID 322956Notes

Reaction equation

HRID 322956 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[C:20](O)([CH3:23])([CH3:22])[CH3:21].CC(=C)C>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:14])[CH2:9][CH2:10][C:11]([O:13][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:12]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 8255Isobutylene2×HCID 2452694-(2-methylphenyl)-4-oxobutanoic acid

Product 1

HCID 10634286HCID 10634286, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-(2-methylphenyl)-4-oxobutanoic acid (40 g), concentrated sulphuric acid (4 mL) and t-butanol (4 mL) in dichloromethane (200 mL) is cooled to 0° C., and isobutylene (about 400 mL) is condensed into the mixture. It is then stirred at 0° C. until t.l.c. shows reaction is complete. The excess isobutylene is allowed to evaporate, and then the mixture is treated carefully with saturated aqueous sodium bicarbonate solution (200 mL), with vigorous stirring. The organic layer is separated, filtered through a pad of silica gel with the aid of more dichloromethane, and concentrated in vacuo, to give t-butyl 4-(2-methylphenyl)-4-oxobutanoate (5 g), in the form of a pale yellow oil.

Workup

  1. customcondensed into the mixture
  2. customshows reaction
  3. customto evaporate
  4. additionthe mixture is treated carefully with saturated aqueous sodium bicarbonate solution (200 mL), with vigorous stirring
  5. customThe organic layer is separated
  6. filtrationfiltered through a pad of silica gel with the aid of more dichloromethane
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1f6ea63657446f5ad236afa14619f6c
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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