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

HRID 1017640Notes

Reaction equation

HRID 1017640 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 over 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 over MgSO4, filtered and concentrated in vacuo to give the desired acid (1.5 g, 87%). 1H NMR (300 MHz, DMSO) δ12.80, 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 over 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 over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ea3ae5b772b42569a3448cd5f1983cb
Source dataset
uspto-grants-2002_11
Patent number
US06479510B2

Reaction notes

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