Ethanol → Benzeneacetic acid, 4-chloro-alpha-(4-chlorophenyl)-, ethyl ester

HRID 2078121Notes

Reaction equation

HRID 2078121 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:24][CH2:25]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[C:9]([O:11][CH2:24][CH3:25])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 6730Bis(4-chlorophenyl)acetic acid

Product 1

HCID 101291Benzeneacetic acid, 4-chloro-alpha-(4-chlorophenyl)-, ethyl ester

Conditions

Temperature
100 °C

Procedure

To a solution of bis(4-chlorophenyl)acetic acid (5.00 g, 17.8 mmol) in EtOH (100 mL) in a 500 mL round bottom flask, was added H2SO4, 36N (0.0988 mL, 1.78 mmol). The mixture was stirred at 100° C. for 18 hours. The mixture was then concentrated in vacuo, diluted with EtOAc (200 mL), and washed with deionized water (3×100 mL) and then with brine (100 mL). The organic layer was dried over MgSO4, concentrated, and dried in vacuo to give the crude product ethyl 2,2-bis(4-chlorophenyl)acetate (5.473 g). MS m/e=309 (M+H)+.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. additiondiluted with EtOAc (200 mL)
  3. washwashed with deionized water (3×100 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8df68022789849f3b72c9b03d9ab1e1f
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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