4-Iodophenol → 1-Iodo-4-propoxybenzene

A mixture of 4-iodophenol (6.6 g), 1-iodopropane (5.1 g), anhydrous potassium carbonate (13.8 g) and acetone (100 ml) was stirred at reflux for 6 hours. Two further portions of 1-iodopropane were added after one hour (5.1 g) and two hours (5.1 g). The acetone was removed by evaporation, the residue was treated with water (100 ml) and the mixture extracted with dichloromethane (2×30 ml). The organic extracts were combined, dried (MgSO4) and evaporated. The residue, an oil, was distilled at 150° C. and 0.5 mm pressure (using a Kugelrohr oven) to give 4-n-propoxyiodobenzene as a colourless oil (7.2 g), NMR(CDCl3): 0.9-1.08(3H,t), 1.7-1.9(2H,m), 3.82-3.92(2H,t), 6.62-6.72(2H,d), 7.5-7.6(2H,d); m/z 262 (M).

1. temperatureat reflux for 6 hours
2. customThe acetone was removed by evaporation
3. additionthe residue was treated with water (100 ml)
4. extractionthe mixture extracted with dichloromethane (2×30 ml)
5. dry with materialdried (MgSO4)
6. customevaporated
7. distillationThe residue, an oil, was distilled at 150° C.

ORD record

ord-9dff3848a8c5455ea8344e7dbfbdd76b

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05691349