O-Cresol → HCID 54248310, compound

HRID 1873990Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:18]1([CH3:25])[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N1C=CN=C1)CCC.CCCCCCCCCCCCCC>[Cu]Cl.C(OCC)C.O.C1(C)C=CC=CC=1>[C:18]1([CH3:25])[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=1[O:24][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

278 μL (2 mmol) 1-bromonaphthaline, 20 mg (0.2 mmol) copper(I) chloride, 550 mg (4 mmol) potassium carbonate, 260 mg (2.4 mmol) o-cresol, 130 μL 1-butylimidazole, 2 mL toluene and 200 μL internal standard (tetradecane) were added to an Ace pressure tube under argon and heated to 120° C. for 16 h. After cooling, water and diethyl ether were added, the organic phase was washed with 10% K2CO3 solution, water and brine and dried over Na2SO4. GC analysis of the organic phase showed a yield of 89%. After evaporation of the solvents, the dark brown oil was submitted to column chromatography over silica gel, eluent light petroleum. 0.38 g of colourless oil was recovered (81% isolated yield). The substance was identified by gc/ms and nmr spectroscopy.

Workup

temperatureAfter cooling
washthe organic phase was washed with 10% K2CO3 solution, water and brine
dry with materialdried over Na2SO4
customAfter evaporation of the solvents
custom0.38 g of colourless oil was recovered
custom(81% isolated yield)

Sources & evidence

ORD record: ord-e953aa7c7cca4ce88a59ec7181f2527c
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304550B2

Reaction notes

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