Hydrogen Peroxide → 5-(5-Hydroxy-4-methyl-4-phenylpentylsulfinyl)-2-methyl-2-phenylpentan-1-ol

HRID 1838105Notes

Reaction equation

HRID 1838105 reaction equation
[OH:1][CH2:2][C:3]([CH3:27])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH2:9][CH2:10][C:11]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:12][OH:13].OO.ClCCl.C(OCC)(=[O:35])C>C(O)(=O)C>[OH:1][CH2:2][C:3]([CH3:27])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:4][CH2:5][CH2:6][S:7]([CH2:8][CH2:9][CH2:10][C:11]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:12][OH:13])=[O:35]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 101569975-(5-Hydroxy-4-methyl-4-phenylpentylsulfanyl)-2-methyl-2-phenylpentan-1-olHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 100925345-(5-Hydroxy-4-methyl-4-phenylpentylsulfinyl)-2-methyl-2-phenylpentan-1-olYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-(5-hydroxy-4-methyl-4-phenylpentylsulfanyl)-2-methyl-2-phenylpentan-1-ol (3.37 g, 8.14 mmol) in glacial acetic acid (100 mL) was added 50% aqueous hydrogen peroxide solution (0.55 g, 8.14 mmol) drop-wise at rt over 5 min. The reaction mixture was stirred at rt for 3 h, while the reaction progress was monitored by TLC (dichloromethane/ethyl acetate=2/1). The reaction mixture was concentrated to yield a crude product (3.5 g) that was purified by column chromatography on silica gel (dichloromethane, then dichloromethane/ethyl acetate=1/1, followed by dichloromethane/ethanol=1/1). The product-containing fractions were concentrated and dried at 120° C. under high vacuo for 2.5 h to give 5-(5-hydroxy-4-methyl-4-phenylpentylsulfinyl)-2-methyl-2-phenylpentan-1-ol (2.55 g, 71%) as colorless, viscous oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 7.30 (m, 8 H), 7.20 (m, 2 H), 3.66-3.56 (m, 4 H), 2.54-2.38 (m, 4 H), 2.13 (br., 2 H), 1.90-1.43 (m, 8 H), 1.33 (s, 6 H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 144.56, 128.68, 126.66, 126.62, 126.62, 71.82, 71.57, 52.92, 43.38, 43.35, 37.56, 37.43, 22.14, 21.77, 17.87, 17.71. HRMS (LSIMS, gly): Calcd. for C24H35O3S1 (MH+): 403.2307, found: 403.2295.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto yield a crude product (3.5 g) that
  3. customwas purified by column chromatography on silica gel (dichloromethane
  4. concentrationThe product-containing fractions were concentrated
  5. customdried at 120° C. under high vacuo for 2.5 h

Sources & evidence

ORD record
ord-84c0099fe85f41e489a12e2bb09fdb6e
Source dataset
uspto-grants-2004_01
Patent number
US06673780B2

Reaction notes

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