Phenol → HCID 4860732, compound

HRID 1357004Notes

Reaction equation

HRID 1357004 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5]

Participants

5

Reactant 3

HCID 996PhenolHCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chloride

Product 1

HCID 4860732HCID 4860732, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A: To a cooled (ice bath) solution of 2,4-dichlorobenzoyl chloride (5 mL, 35.66 mmol) in 50 mL CH2Cl2 was added phenol (3.13 mL, 35.66 mmol), followed by triethylamine (4.97 mL, 35.66 mmol). The resulting reaction mixture was stirred at room temperature for 5 h. The mixture was then partitioned between CH2Cl2 and water. The organic layer was dried (Na2SO4), filtered, and evaporated in vacuo to yield 9.5 g of phenyl 2,4-dichlorobenzoate. MS (NH3—CI) 284 (M+NH4)+.

Workup

  1. customThe resulting reaction mixture
  2. customThe mixture was then partitioned between CH2Cl2 and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-baf1b05ee5204fe1a8a7cfc775b7c23b
Source dataset
uspto-grants-2003_07
Patent number
US06589958B1

Reaction notes

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