Sulfuric Acid → HCID 67099452, compound

HRID 1868797Notes

Reaction equation

HRID 1868797 reaction equation
OS(O)(=O)=O.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]([CH3:29])([CH3:28])[C:15]([CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20]CC)=O)=[O:16])[CH:10]=[CH:11][C:12]=1[Cl:13]>CCOC(C)=O>[Cl:13][C:12]1[CH:11]=[C:10]2[C:9](=[CH:8][C:7]=1[Cl:6])[C:14]([CH3:29])([CH3:28])[C:15](=[O:16])[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:18]2[OH:20]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67099354HCID 67099354, compound

Product 1

HCID 67099452HCID 67099452, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Concentrated H2SO4 (52.5 mL, 621 mmol) was added dropwise via an addition funnel to diethyl 2-(2-(3,4-dichlorophenyl)-2-methylpropanoyl)malonate (11.66 g, 31.1 mmol) cooled to 0° C. The reaction mixture was allowed to slowly warm to ambient temperature and then poured into a beaker of ice, diluted with 200 mL of EtOAc, added to a separatory funnel, partitioned with water, washed 2 times with 50 mL of water, separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (9.61 g) as a white amorphous solid. MS (m/z)=329 (M+H)+.

Workup

  1. temperatureto slowly warm to ambient temperature
  2. additionpoured into a beaker of ice
  3. additionadded to a separatory funnel
  4. custompartitioned with water
  5. washwashed 2 times with 50 mL of water
  6. customseparated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd2dc320d40e4e3eb9d8d7cd33a1eb71
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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