1,10-Phenanthroline → 1-Heptoxy-3,5-dimethylbenzene

Participants

Role	Name	HCID	Charge
Reactant	1,10-Phenanthroline	HCID 1318	—
Reactant	Heptanol	HCID 8129	—
Reactant	Dodecane	HCID 8182	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-Iodo-3,5-dimethylbenzene	HCID 140924	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	O-Xylene	HCID 7237	—
Product	1-Heptoxy-3,5-dimethylbenzene	HCID 15531005	64%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A screw cap test tube was charged with n-heptanol (283 μL, 2.00 mmol), 3,5-dimethyliodobenzene (144 μL, 1.00 mmol), CuI (4.75 mg, 0.025 mmol), 1,10-phenanthroline (1.80 mg, 0.01 mmol), Cs2CO3 (977 mg, 3.00 mmol) and o-xylene (1 mL). The test tube was sealed with a screw cap. The reaction mixture was stirred magnetically and heated at 120° C. for 19 hours. The reaction mixture was allowed to reach room temperature. Dodecane (227 μL, 1.00 mmol; internal standard) was added and a GC sample was filtered through Celite and eluted with CH2Cl2. GC analysis revealed 64% yield of the desired product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06867298B2
Source dataset	uspto-grants-2005_03
ORD ID	ord-9c03d02167134c72857d7aac06272e46
Source note	uspto-grants-2005_03