Hydrogen Peroxide → HCID 9980142, compound

HRID 1838104Notes

Reaction equation

HRID 1838104 reaction equation
[OH:1][CH2:2][C:3]([CH3:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:4][CH2:5][CH2:6][CH2:7][S:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:14][OH:15].[OH:30]O>C(O)(=O)C.O>[OH:1][CH2:2][C:3]([CH3:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:4][CH2:5][CH2:6][CH2:7][S:8]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:14][OH:15])=[O:30]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 102018946-(6-Hydroxy-5-methyl-5-phenylhexylsulfanyl)-2-methyl-2-phenylhexan-1-ol

Product 1

HCID 9980142HCID 9980142, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 6-(6-hydroxy-5-methyl-5-phenylhexylsulfanyl)-2-methyl-2-phenylhexan-1-ol (3.0 g, 7.0 mmol) in glacial acetic acid (20 mL) was added hydrogen peroxide (50 wt. % in water; 0.5 mL, 7.0 mmol). The reaction mixture was stirred at rt for 22 h, then diluted with water (100 mL), and extracted with chloroform (3×80 mL). The combined organic phases were subsequently washed with saturated NaHCO3 solution (3×80 mL) and saturated NaCl solution (80 mL), dried over MgSO4, concentrated in vacuo, and dried in high vacuo to give crude 6-(6-hydroxy-5-methyl-5-phenylhexylsulfinyl)-2-methyl-2-phenylhexan-1-ol (2.63 g 88%) as an oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 7.42-7.12 (m, 10 H), 3.78-3.58 (m, 2 H), 3.58-3.45 (m, 2 H), 2.90-2.70 (m, 2 H), 2.68-2.39 (m, 2 H), 1.95-1.50 (m, 8 H), 1.50-1.00 (m, 10 H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 144.5, 144.4, 128.4, 128.3, 126.5, 126.2, 126.1, 72.2, 72.1, 71.9, 52.4, 52.0, 43.2, 37.8, 37.7, 23.2, 22.9, 22.4, 21.7, 21.5. HRMS (LSIMS, nba): Calcd. for C26H39O3S1 (MH+): 431.2620, found: 431.2611.

Workup

  1. extractionextracted with chloroform (3×80 mL)
  2. washThe combined organic phases were subsequently washed with saturated NaHCO3 solution (3×80 mL) and saturated NaCl solution (80 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customdried in high vacuo

Sources & evidence

ORD record
ord-28addaa683364c11b6fd15cb8449c4a4
Source dataset
uspto-grants-2004_01
Patent number
US06673780B2

Reaction notes

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