Sodium Hydroxide → 6-(5-Carboxy-5-phenyl-hexylsulfanyl)-2-methyl-2-phenyl-hexanoic acid

HRID 48316Notes

Reaction equation

HRID 48316 reaction equation
C([O:3][C:4](=[O:35])[C:5]([CH3:34])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:23]([O:25]CC)=[O:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])C.[OH-].[Na+]>C(O)C.O>[C:4]([C:5]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:34])[CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:16])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]([OH:25])=[O:24])([OH:35])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 116418176-(5-Ethoxycarbonyl-5-phenylhexylsulfanyl)-2-methyl-2-phenylhexanoic acid ethyl ester

Product 1

HCID 102971706-(5-Carboxy-5-phenyl-hexylsulfanyl)-2-methyl-2-phenyl-hexanoic acidYield 68.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 6-(5-ethoxycarbonyl-5-phenylhexylsulfanyl)-2-methyl-2-phenylhexanoic acid ethyl ester (6.00 g, 12.0 mmol) and sodium hydroxide (3.1 g, 74.0 mmol) in ethanol (40 mL) and deionized water (4 mL) was heated to reflux for 2 h. The ethanol was evaporated in vacuo and the residue was dissolved in water (20 mL) and extracted with diethyl ether (20 mL). The organic phase was discarded. The aqueous layer was acidified with 2 N hydrochloric acid (15 ml) to pH 2-3 and extracted with diethyl ether (4′ 50 mL). The combined organic layers were washed with brine (15 mL), dried over MgSO4, and concentrated in vacuo. The residue (4.53 g) was purified by column chromatography on silica gel (hexanes/ethyl acetate=10/1) to give 6-(5-carboxy-5-phenyl-hexylsulfanyl)-2-methyl-2-phenyl-hexanoic acid (3.63 g, 68%) as a yellowish oil. 1H NMR (300 MHz, CDCl3/TMS): d (ppm): 7.42-7.20 (m, 10H), 2.45 (t, J=7.3 Hz, 4H), 2.15-1.80 (m, 4H), 1.65-1.45 (m, 4H), 1.56 (s, 6H), 1.40-1.15 (m, 4H). 13C NMR (75 MHz, CDCl3/TMS): d (ppm): 182.43, 142.89, 128.41, 126.91, 126.05, 50.00, 38.53, 31.80, 30.00, 24.03, 22.40. HRMS (LSIMS, nba): Calcd. for C26H35O4S1 (MH+): 443.2256, found: 443.2231.

Workup

  1. temperatureto reflux for 2 h
  2. customThe ethanol was evaporated in vacuo
  3. dissolutionthe residue was dissolved in water (20 mL)
  4. extractionextracted with diethyl ether (20 mL)
  5. extractionextracted with diethyl ether (4′ 50 mL)
  6. washThe combined organic layers were washed with brine (15 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue (4.53 g) was purified by column chromatography on silica gel (hexanes/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-78e05ab6bfa14117b27204f62c1b9645
Source dataset
uspto-grants-2004_03
Patent number
US06703422B2

Reaction notes

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