Hydrochloric Acid → HCID 18790156, compound

HRID 1107120Notes

Reaction equation

HRID 1107120 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([CH:14]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]([O:17]C)=[O:16])(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([CH:14]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:15]([OH:17])=[O:16])(=[O:12])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18790140HCID 18790140, compound

Product 1

HCID 18790156HCID 18790156, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-[(3,4-dimethoxyphenyl)sulfonyl]-6-phenylhexanoate (1.3 g, 3.2 mmol) and 10% sodium hydroxide (15 mL) in ethanol (15 mL) is heated under reflux for 20 minutes. The solution is cooled and is added to aqueous HCl and is extracted with ether. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo and the residue is dissolved in ethyl acetate and the solution is diluted with hexane to precipitate 2-[(3,4-dimethoxyphenyl)sulfonyl]-6-phenylhexanoic acid (0.5 g, 40%): m.p. 114-16° C. Anal. (C20H24O6S) C, H: 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.28-1.48 (m, 2H), 1.54-1.70 (m, 2H), 1.87-2.05 (m, 2H), 2.48-2.64 (m, 2H), 3.88 (d, 7H), 6.97 (d, 1H), 7.12-7.20 (m, 2H), 7.20-7.30 (m, 4H), 7.40-7.50 (m, 1H).

Workup

  1. temperatureunder reflux for 20 minutes
  2. temperatureThe solution is cooled
  3. extractionis extracted with ether
  4. washThe organic layer is washed with water
  5. dry with materialis dried over MgSO4
  6. customThe solvent is removed in vacuo
  7. dissolutionthe residue is dissolved in ethyl acetate
  8. additionthe solution is diluted with hexane
  9. customto precipitate 2-[(3,4-dimethoxyphenyl)sulfonyl]-6-phenylhexanoic acid (0.5 g, 40%)

Sources & evidence

ORD record
ord-847ff5c688594b7386f4f971bb65b918
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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