tert-Butyl hydroperoxide → HCID 69936115, compound

HRID 1265260Notes

Reaction equation

HRID 1265260 reaction equation
[Se](=O)=O.C([O:8]O)(C)(C)C.[CH3:10][C:11]1([CH3:30])[CH2:20][CH2:19][C:18]([CH3:22])([CH3:21])[C:17]2[CH:16]=[C:15]([C:23]([CH3:25])=[CH2:24])[C:14]([O:26][CH2:27][CH2:28][CH3:29])=[CH:13][C:12]1=2.CCCCCC>ClCCl>[CH3:10][C:11]1([CH3:30])[CH2:20][CH2:19][C:18]([CH3:21])([CH3:22])[C:17]2[CH:16]=[C:15]([C:23]([CH3:25])=[CH:24][OH:8])[C:14]([O:26][CH2:27][CH2:28][CH3:29])=[CH:13][C:12]1=2

Participants

6

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 8058HexaneHCID 24007Selenium DioxideHCID 18615027HCID 18615027, compound

Product 1

HCID 69936115HCID 69936115, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 5 mL round-bottom flask was introduced selenium dioxide (71 mg, 0.64 mmol), 1 mL of dichloromethane, and 90% t-butyl hydroperoxide (0.284 mL, 2.56 mmol). After the mixture had been stirred for 30 min. at room temperature, 2-(5,5,8,8-tetramethyl-3-propyloxy-5,6,7,8-tetrahydronaphthalen-2-yl)-propene (366 mg, 1.28 mmol), in 1 mL of dichloromethane was slowly added. The mixture was stirred at room temperature for 3 h. Then quenched with aqueous saturated NaHCO3. The mixture was extracted with dichloromethane (2×10 mL), washed with water (10 mL) and brine (10 mL), and the combined organic phase dried (Na2SO4). Concentrated in vacuo to give an oil which was subjected to chromatography (10% EtOAC/90% hexane) to give 149 mg (40%) of 2-(5,5,8,8-tetramethyl-3-propyloxy-5,6,7,8-tetrahydro naphthalen-2-yl)-propen-1-ol. 1H NMR (400 MHz, (CDCl3) δ 7.14(s, 1H, aromatic), 6.76(s, 1H, aromatic), 5.36(s, 1H, vinylic), 5.22(s, 1H, vinylic), 4.44(d, J=6.1 Hz, CH2OH), 3.93(t, J=6.5 Hz, 2H, CH2), 2.19(t, J=6.1 Hz, 1H, OH), 1.82(sx, J=6.8 Hz, 2H, CH2), 1.66(s, 4H, 2CH2), 1.28(s, 6H, 2CH3), 1.26(s, 3H, CH3), 1.25(s, 3H, CH3) and 1.03(t, J=7.3 Hz, 3H, CH3).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. customThen quenched with aqueous saturated NaHCO3
  3. extractionThe mixture was extracted with dichloromethane (2×10 mL)
  4. washwashed with water (10 mL) and brine (10 mL)
  5. dry with materialthe combined organic phase dried (Na2SO4)
  6. concentrationConcentrated in vacuo
  7. customto give an oil which

Sources & evidence

ORD record
ord-00fe048dd7ac48a0bc7cabe30cc448e4
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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