Methylparaben → Methyl 4-hydroxy-3-iodobenzoate

Temperature

45 °C

To a 500 mL 3-necked flask equipped with a magnetic stirrer, a thermometer, and a condenser were added 10.0 g of methyl 4-hydroxybenzoate (Aldrich) and 30 mL of glacial acetic acid. To this suspension was added a solution of 11.74 g of iodine monochloride in 30 mL of glacial acetic acid via addition funnel. The solution was heated at 80° C. for 1 h, 45° C. for 18 h, and 90° C. for an additional 4 h. Cooling to RT afforded a thick red-orange suspension which was transferred to a 1 L separatory funnel and dissolved in 500 mL of CHCl3 by shaking vigorously. The dark purple solution was washed with water (2×100 mL), saturated aqueous sodium thiosulfate (2×100 mL), and 5% aqueous NaHCO3 (2×100 mL). A light yellow solution resulted which was dried over MgSO4, and concentrated in vacuo to give a white solid. This material was recrystallized from water-MeOH to afford 14.92 g (82%) of methyl 4-hydroxy-3-iodobenzoate as a white crystalline solid, m.p. 145-146° C.

1. customTo a 500 mL 3-necked flask equipped with a magnetic stirrer
2. additionvia addition funnel
3. temperatureCooling to RT
4. customafforded a thick red-orange suspension which
5. customwas transferred to a 1 L separatory funnel
6. washThe dark purple solution was washed with water (2×100 mL), saturated aqueous sodium thiosulfate (2×100 mL), and 5% aqueous NaHCO3 (2×100 mL)
7. customA light yellow solution resulted which
8. dry with materialwas dried over MgSO4
9. concentrationconcentrated in vacuo
10. customto give a white solid
11. customThis material was recrystallized from water-MeOH

ORD record

ord-51e1673e275646c3a01c7fa51ca761bf

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06319702B1