Hydrochloric Acid → 2-[4-(Methanesulfonyloxy)phenyl]acetic acid

HRID 1628132Notes

Reaction equation

HRID 1628132 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=1.[Li+].[OH-].Cl.CCOC(C)=O>O1CCOCC1.O>[CH3:15][S:12]([O:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:16])=[O:2])=[CH:10][CH:9]=1)(=[O:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 116156834-[(Methoxycarbonyl)methyl]phenyl mesylate

Product 1

HCID 288754632-[4-(Methanesulfonyloxy)phenyl]acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

(4-Methanesulfonyloxy-phenyl)-acetic acid methyl ester (615 mg, 2.51 mmol) was dissolved in a 1:1 mixture of dioxane and water (6 mL) and an aq. solution of LiOH (2 eq., 5.05 mL, 1N) was added and the mixture was stirred at ambient temperature for 15 min. After the addition of aq. HCl (3N) and EtOAc, the phases were separated and the organic layer was dried (MgSO4), filtered and evaporated under reduced pressure. The title compound was obtained without further purification as a solid (497 mg, 85.7%). 1H NMR (400 MHz, CDCl3): δ 7.35-7.38 (d, 2H), 7.25-7.29 (d, 2H), 3.64 (s, 2H), 3.19 (s, 3H).

Workup

  1. customthe phases were separated
  2. dry with materialthe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-28b8bfad16c7494ca0bcf9cc4cb7760e
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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