Isobutylene → 4-(4'-Hydroxyphenyl)-2-butanone

HRID 1165353Notes

Reaction equation

HRID 1165353 reaction equation
C([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14](=[O:16])[CH3:15])=[CH:8][CH:7]=1)(C)(C)C.CC(=C)C.[OH-].[Na+]>S(=O)(=O)(O)O>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14](=[O:16])[CH3:15])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8255IsobutyleneHCID 14798Sodium HydroxideHCID 19862979HCID 19862979, compound

Product 1

HCID 216484-(4'-Hydroxyphenyl)-2-butanoneYield 93%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

100 g (0.45 mole) of 1-(4-tert.-butoxy-phenyl)-butan-3-one are suspended in 250 ml of 2N sulfuric acid and the mixture is refluxed for about 3 hours, with vigorous stirring. The course of the reaction can be followed by measuring the isobutylene liberated. After completion of the reaction, the mixture is cooled to room temperature and brought to pH 6 with dilute sodium hydroxide solution, after which the product crystallizes out in about 95% purity. It is isolated by filtering off or centrifuging (73 g of 95% pure material; yield 93%), and is recrystallized from water/ethanol.

Workup

  1. temperaturethe mixture is refluxed for about 3 hours, with vigorous stirring
  2. customThe course of the reaction
  3. customAfter completion of the reaction
  4. customafter which the product crystallizes out in about 95% purity
  5. customIt is isolated
  6. filtrationby filtering off
  7. customis recrystallized from water/ethanol

Sources & evidence

ORD record
ord-4983e5a2ead247dc9315796a4834c222
Source dataset
uspto-grants-1990_03
Patent number
US04908481

Reaction notes

Loading…