Water → 3-[(1S)-2-tert-Butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoic acid

HRID 644093Notes

Reaction equation

HRID 644093 reaction equation
[C:1]([O:5][CH2:6][C@H:7]([CH3:28])[O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH:16]=1)[C:12]#N)([CH3:4])([CH3:3])[CH3:2].[OH2:29].[OH-:30].[Na+]>C(O)C>[C:1]([O:5][CH2:6][C@H:7]([CH3:28])[O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH:16]=1)[C:12]([OH:30])=[O:29])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 592633083-[(1S)-2-tert-Butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzonitrile

Product 1

HCID 592633093-[(1S)-2-tert-Butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoic acidYield 69.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-[(1S)-2-tert-Butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzonitrile (23.7 mmol; 9.56 g) was dissolved in ethanol (95.60 ml), and transferred to a 250 ml round bottomed flask, using ethanol (5 ml) to wash the residual solid from the flask. Water (6.25 ml) and sodium hydroxide (118.5 mmol; 6.30 ml) was added and the reaction was heated to reflux for 18 hours. The ethanol was removed in vacuo. The residual yellow suspension was dissolved in MTBE (162.5 ml) and water (162.5 ml). The two layers were separated, the MTBE layer was discarded and the aqueous layer was acidified with 2M HCl (100 ml). The aqueous layer was extracted twice with MTBE (162.5 ml). The organic extracts were combined and dried with magnesium sulfate, the MTBE was removed in vacuo, to give the desired product (7.0 g, 69.9% yield).

Workup

  1. customtransferred to a 250 ml round bottomed flask
  2. washto wash the residual solid from the flask
  3. temperaturethe reaction was heated
  4. temperatureto reflux for 18 hours
  5. customThe ethanol was removed in vacuo
  6. dissolutionThe residual yellow suspension was dissolved in MTBE (162.5 ml)
  7. customThe two layers were separated
  8. extractionThe aqueous layer was extracted twice with MTBE (162.5 ml)
  9. dry with materialdried with magnesium sulfate
  10. customthe MTBE was removed in vacuo

Sources & evidence

ORD record
ord-2d39752a1e0b4611b5aed42f6817f339
Source dataset
uspto-grants-2010_04
Patent number
US07700640B2

Reaction notes

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