Hydrochloric Acid → (R)-4-chloro-1-(3,5-dimethylphenyl)-3-methylbutan-1-one

HRID 1275185Notes

Reaction equation

HRID 1275185 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([CH3:17])[CH:16]=1)[C:5]([C@H:7]1[CH:11]([CH3:12])[CH2:10]OC1=O)=[O:6].[ClH:18].C(=O)(O)[O-].[Na+]>>[Cl:18][CH2:10][C@H:11]([CH3:12])[CH2:7][C:5]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:16]=[C:15]([CH3:17])[CH:14]=1)=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2×HCID 53860757(R)-3-(3,5-dimethylbenzoyl)-4-methyldihydrofuran-2-one

Product 1

HCID 53672991(R)-4-chloro-1-(3,5-dimethylphenyl)-3-methylbutan-1-one

Procedure

To a solution of (R)-3-(3,5-dimethylbenzoyl)-4-methyldihydrofuran-2-one (2.42 g in 15 mL dioxane) was added 15 mL conc. hydrochloric acid and the mixture heated to reflux on an oil bath. After one hour, the reaction was poured into cold, saturated aqueous sodium bicarbonate. Additional solid sodium bicarbonate was added until all acid was neutralized. This was then extracted with ethyl acetate, washed with brine. Concentration in vacuo provided the title compound (2.12 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. extractionThis was then extracted with ethyl acetate
  4. washwashed with brine
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-416ee6ec866d44078a574ba1abe4bd43
Source dataset
uspto-grants-2000_12
Patent number
US06159989

Reaction notes

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