Sodium Hydroxide → [(4-Methylbenzene-1-sulfonyl)oxy]acetic acid

HRID 2422920Notes

Reaction equation

HRID 2422920 reaction equation
[S:1]([O:11][CH2:12][C:13]([O:15]CC)=[O:14])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[OH-].[Na+]>C(O)C>[S:1]([O:11][CH2:12][C:13]([OH:15])=[O:14])([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11821264Ethyl 2-(p-Toluenesulfonyloxy)acetate

Product 1

HCID 226266[(4-Methylbenzene-1-sulfonyl)oxy]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(tosyloxy)acetate (2, 860 mg, 3.33 mmol) in ethanol (4 ml) was treated at room temperature with 5% NaOH aqueous solution (2 ml). The resulting mixture was stirred at room temperature for 3 h. The ethanol was removed in vacuo and aqueous 5% HCl solution (2.7 ml) was added. The aqueous mixture was extracted with chloroform and the organic extracts dried (Na2SO4), filtered and the solvent removed under reduced pressure. The remaining white solid was recrystallized from hexane/ethyl acetate as a white powder (476 mg, 62%). [This reaction was repeated on 2× scale (1.449 g, 94%)]. δH (400 MHz, MeOD) 2.45 (3H, s, Me), 4.58 (2H, s, CH2), 7.44 (2H, d, J=8.2 Hz, ArH), 7.82 (2H, d, J=8.2 Hz, ArH); δc (100.6 MHz, MeOD) 20.4, 64.7, 128.0, 129.9, 133.0, 145.6, 168.2; MS (ES+) 247.8 (100%, [M+H2O]+); MS (ES−) 170.1 (100%, TsO−).

Workup

  1. customThe ethanol was removed in vacuo and aqueous 5% HCl solution (2.7 ml)
  2. additionwas added
  3. extractionThe aqueous mixture was extracted with chloroform
  4. dry with materialthe organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe remaining white solid was recrystallized from hexane/ethyl acetate as a white powder (476 mg, 62%)

Sources & evidence

ORD record
ord-a0dc166af4a84344839a951390973bd9
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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