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Dichlorophen → [4-Chloro-2-(5-chloro-2-hydroxy-benzyl)-phenoxy]-acetic acid benzyl ester

HRID 2244470
Notes
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Reaction equation

HRID 2244470 reaction equation
[CH2:1]([C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[OH:17])[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[Li+].[Li+].[CH2:24]([O:31][C:32](=[O:35])[CH2:33]Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH2:24]([O:31][C:32](=[O:35])[CH2:33][O:17][C:11]1[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=1[CH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3037DichlorophenHCID 11125Lithium CarbonateHCID 62576Benzyl bromoacetate2×

Product 1

HCID 68450956[4-Chloro-2-(5-chloro-2-hydroxy-benzyl)-phenoxy]-acetic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2,2′-Methylene-bis(4-chloro-phenol) (12 g, 44.6 mmol) is dissolved in DMF (100 mL). Lithium carbonate (3.3 g, 44.6 mmol) is added, followed by benzyl-2-bromoacetate (7.7 mL, 49 mmol). The suspension is stirred at 80° C. for 8 hours. Further benzyl-2-bromoacetate (1 mL, 6.4 mmol) is added and stirring continued at 100° C. for 4 hours. The reaction mixture is evaporated to dryness, water is added to the residue which is acidified to pH 1 with 2 M aqueous HCl and extracted with EtOAc. The organic layer is washed with brine, dried (MgSO4) and evaporated. The crude product is purified by flash column chromatography over silica gel eluting with 4:1 iso-hexane:EtOAc. The product is suspended in iso-hexane, dissolved in the minimum volume of EtOAc, seeded and left to stand. The resultant solid is collected by filtration, washed with iso-hexane and dried to give [4-chloro-2-(5-chloro-2-hydroxy-benzyl)-phenoxy]-acetic acid benzyl ester; m.p.=135-137° C.

Workup

  1. stirringstirring
  2. waitcontinued at 100° C. for 4 hours
  3. customThe reaction mixture is evaporated to dryness, water
  4. additionis added to the residue which
  5. extractionextracted with EtOAc
  6. washThe organic layer is washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe crude product is purified by flash column chromatography over silica gel eluting with 4:1 iso-hexane
  10. dissolutiondissolved in the minimum volume of EtOAc
  11. waitleft
  12. filtrationThe resultant solid is collected by filtration
  13. washwashed with iso-hexane
  14. customdried

Sources & evidence

ORD record
ord-cca656725cc54e928622e126dd72dd33
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07678826B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes