Hexane → HCID 131732796, compound

HRID 1476368Notes

Reaction equation

HRID 1476368 reaction equation
[C:1]([C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][C:19]([O:23][CH3:24])=[CH:20]2)=[CH:15][CH:14]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CCCCCC>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][C:19]([O:23][CH3:24])=[CH:20]2)=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 8058HexaneHCID 131732797HCID 131732797, compound

Product 1

HCID 131732796HCID 131732796, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent2×

Procedure

Using 7-methoxy-2-naphthyltrifluoromethanesulfonate (30.63 g, 0.10 mol) and 1-dodecyne (20.79 g, 0.125 mol), 7-dodecyn-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-dodecyn-1-yl-2-methoxynaphthalene (32.0 g, quantitative). The obtained 7-dodecyn-1-yl-2-methoxynaphthalene (total amount) was subjected to catalytic reduction in toluene (316 ml) under a hydrogen atmosphere by adding 10% Pd/C (2.11 g). The obtained product was subjected to column chromatography (silica gel, developed with a mixture of toluene and hexane) to obtain 7-dodecyl-2-methoxynaphthalene (compound (3)-14, 31.10 g, yield of 96%).

Sources & evidence

ORD record
ord-704b1a48b26c4b38a9973be475de8d89
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

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