Acetyl chloride → 4-(4-Acetoxyphenoxy)benzoic acid

HRID 23373Notes

Reaction equation

HRID 23373 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][C:6]1[CH:21]=[CH:20][C:9]([O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1>C(Cl)Cl>[C:1]([O:5][C:6]1[CH:21]=[CH:20][C:9]([O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 6155424-(4-Hydroxy-phenoxy)-benzoic acid

Product 1

HCID 225734654-(4-Acetoxyphenoxy)benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetylchloride (1.5 mL, 21 mmol) is added to a solution of 4-(4-hydroxyphenoxy)benzoic acid (2.3 g, 10 mmol) and TEA (2.9 mL, 21 mmol) in CH2Cl2 (50 mL). The reaction is stirred for 16 hours at room temperature. The reaction mixture is diluted with CH2Cl2 and washed three times with saturated NaHCO3. The organic layer is dried (MgSO4), filtered and concentrated in vacuo. The resulting material is dissolved in dioxane (6 mL). Aqueous LiOH (1N, 930 μL) is added, and the reaction is allowed to stir for one hour at room temperature. The reaction mixture is poured into CH2Cl2 and washed twice with KHSO4. The organic layer is dried (MgSO4), filtered and concentrated in vacuo to give 4-(4-acetoxyphenoxy)benzoic acid (1.5 g, 87%). 1H NMR (300 MHz, DMSO) δ 12.80, 7.96, 7.23-7.13, 7.04, 2.29.

Workup

  1. washwashed three times with saturated NaHCO3
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting material is dissolved in dioxane (6 mL)
  6. additionAqueous LiOH (1N, 930 μL) is added
  7. stirringto stir for one hour at room temperature
  8. additionThe reaction mixture is poured into CH2Cl2
  9. washwashed twice with KHSO4
  10. dry with materialThe organic layer is dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57713b86a77642e28b6eb5f0508e6d42
Source dataset
uspto-grants-2005_02
Patent number
US06852716B2

Reaction notes

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