3,5-Bis-(m-chlorophenyl)4-(2-hydroxyethoxy)benzoic acid ethyl ester → 3,5-Bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid

HRID 1884731Notes

Reaction equation

HRID 1884731 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[C:8]([O:18][CH2:19][CH2:20][OH:21])=[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH:6]=1)C>C1COCC1.C(O)C.[OH-].[K+]>[Cl:17][C:13]1[CH:12]=[C:11]([C:9]2[CH:10]=[C:5]([CH:6]=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C:8]=2[O:18][CH2:19][CH2:20][OH:21])[C:4]([OH:29])=[O:3])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 1

HCID 539906423,5-Bis-(m-chlorophenyl)4-(2-hydroxyethoxy)benzoic acid ethyl ester

Product 1

HCID 222373953,5-Bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acidYield 91%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

Procedure

To a stirred solution of 3,5-bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acid ethyl ester (2.009 g, 4.658 mmol) in THF (30 ml) and ethanol (15 ml) was added IN KOH (9.32 ml). After 20 h, the reaction was concentrated in vac. The residue was diluted with water (40 ml) and acidified with 2N HCl (9.32 ml). After 2 h, the solids were collected, rinsed with water, dissolved in EtOAc, dried over Na2SO4, filtered, concentrated in vac, and the residue dried to give the desired product as a white solid (1.708 g, 91%); mp 184-192 (partial melt), solidifies, and melts 200-202° C.; 1H NMR (300 MHz, DMSO-d6) δ 3.12 (q, J=4 Hz, 2H), 3.28 (t, J=4 Hz, 2H), 4.45 (t, J=4 Hz, 1H), 7.45-7.60 (m, 6H), 7.70 (s, 2H), 7.91 (s, 2H), 13.10 (s, 1H).

Workup

  1. concentrationthe reaction was concentrated in vac
  2. additionThe residue was diluted with water (40 ml)
  3. waitAfter 2 h
  4. customthe solids were collected
  5. washrinsed with water
  6. dissolutiondissolved in EtOAc
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vac
  10. customthe residue dried

Sources & evidence

ORD record
ord-12754d44ce634409aed22c902b949492
Source dataset
uspto-grants-2004_07
Patent number
US06765021B2

Reaction notes

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