Water → 3,3-Bis(p-chlorophenyl)propionic acid

HRID 2265259Notes

Reaction equation

HRID 2265259 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[Al+3].[Cl-:14].[Cl-].[Cl-].O>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([C:2]2[CH:12]=[CH:11][C:5]([Cl:14])=[CH:4][CH:3]=2)[CH2:7][C:8]([OH:10])=[O:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 153712-Propenoic acid, 3-(4-chlorophenyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 756813,3-Bis(p-chlorophenyl)propionic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-chlorocinnamic acid (10.0 g, 54.8 mmol) in chlorobenzene (75 mL) at 0° C. was added AlCl3 (12.0 g, 90 mmol) in 4 portions. The mixture was stirred for 10 min at 0° C. then was warmed to 40° C. and stirred for 1 h. Crushed ice (75 g) was added carefully, followed by water (75 mL). The aqueous layer was extracted with DCM (3×). The combined organic extracts were dried (Na2SO4) and concentrated to provide the crude acid as a tan solid. Recrystallization from EtOH provided 7.81 g (48%) of the desired acid as a pale yellow solid. 1H NMR (400 MHz, CDCl3): 7.31-7.22 (m, 4H), 7.14-7.07 (m, 4H), 4.47 (t, J=8.0, 1H), 3.03 (d, J=7.9, 2H).

Workup

  1. temperaturethen was warmed to 40° C.
  2. stirringstirred for 1 h
  3. extractionThe aqueous layer was extracted with DCM (3×)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customto provide the crude acid as a tan solid
  7. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-a80b401456ed41e399a627eb6196e148
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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