Hexane → HCID 131732794, compound

HRID 1476367Notes

Reaction equation

HRID 1476367 reaction equation
[C:1]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([O:19][CH3:20])=[CH:16]2)=[CH:11][CH:10]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CCCCCC>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([O:19][CH3:20])=[CH:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 8058HexaneHCID 131732795HCID 131732795, compound

Product 1

HCID 131732794HCID 131732794, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent2×

Procedure

Using 7-methoxy-2-naphthyltrifluoromethanesulfonate (30.63 g, 0.10 mol) and 1-octyne (13.78 g, 0.125 mol), 7-octyn-1-yl-2-methoxynaphthalene was synthesized by the same operation as that in the method for synthesizing 7-decyl-2-methoxynaphthalene according to Example 3, and subjected to column chromatography (silica gel, developed with a mixture of toluene and hexane) to obtain a light yellow oil product of 7-octyn-1-yl-2-methoxynaphthalene (22.9 g, yield of 86%). The obtained 7-octyn-1-yl-2-methoxynaphthalene (total amount) was subjected to catalytic reduction in toluene (213 ml) under a hydrogen atmosphere by adding 10% Pd/C (2.13 g). The obtained product was subjected to column chromatography (silica gel, developed with a mixture of toluene and hexane) to obtain 7-octyl-2-methoxynaphthalene (compound (3)-10, 24.30 g, yield of 90%).

Sources & evidence

ORD record
ord-f1234b5c9fd64b81b7cd62a9ff4ca747
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

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