Naphthalene → 1,3-Dioxolan-2-one, 4-hexyl-

HRID 1411122Notes

Reaction equation

HRID 1411122 reaction equation
[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2]1.C1C(=O)N(Br)C(=O)C1.[C:18]([O:26]OC(=O)C1C=CC=CC=1)(=[O:25])C1C=CC=CC=1.C1C2C(=CC=CC=2)C=CC=1>CN(C=O)C>[CH2:4]([CH:3]1[CH2:2][O:26][C:18](=[O:25])[O:1]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 931NaphthaleneHCID 7187Benzoyl PeroxideHCID 181262-HexyloxiraneHCID 67184N-bromobutanimide

Product 1

HCID 110843401,3-Dioxolan-2-one, 4-hexyl-Yield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 5 mL volumetric flask was charged with 1.5 mL of 1,2-epoxyoctane (1a, 10 mmol), 89 mg of NBS (0.5 mmol), 0.12 g of benzoyl peroxide (0.5 mmol), and 0.13 g of naphthalene (1.0 mmol). The volumetric flask was filled to the mark with anhydrous DMF (2 M). An 8 mL, stainless steel Harvard Apparatus syringe was filled with the solution and then attached to the flow apparatus (syringe pump). The flow apparatus itself was set up as described above. After approximately 4 tR's (˜2 h), a sample was taken using the 6-way valve. The sample was analyzed by GC and 1H NMR. GC analysis indicated 96% conversion whereas 1H NMR analysis indicated a yield of 87% of the title compound 2a. IR (neat): 2928, 2859, 1788, 1384, 1165, 1059, 774 cm−1. 1H NMR (400 MHz, CDCl3): δ 4.67 (qd, J=7.5, 5.5 Hz, 1H), 4.50 (t, J=8.1 Hz, 1H), 4.04 (dd, J=8.3, 7.3 Hz, 1H), 1.79-1.73 (m, 1H), 1.68-1.61 (m, 1H), 1.45-1.27 (m, 10H), 0.86 (t, J=6.9 Hz, 3H). 13C NMR (100 MHz, CDCl3): δ 155.1, 77.1, 69.4, 33.9, 31.5, 28.8, 24.3, 22.5. HRMS (DART) m/z calcd for C9H20NO3 [M+NH4]+: 190.1438. Found: 190.1438.

Workup

  1. customAfter approximately 4 tR's (˜2 h)

Sources & evidence

ORD record
ord-be8827882db8413d8303c2632897c2ba
Source dataset
uspto-grants-2014_12
Patent number
US08921580B2

Reaction notes

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