Reaction #312697

Reaction equation

Iodine

isovanillin isopropyl ether

→

title compound

Yield 93.0%

2-Iodo-5-isopropoxy-4-methoxybenzaldehyde

Yield 93.0%

Solvents

chloroform

Conditions

Workup

1. 1
   Temperatureto reflux for a futher 6.5 h
2. 2
   TemperatureThe reaction mixture was then cooled
3. 3
   Filtrationfiltered
4. 4
   Washrinsing with chloroform (50 mL)
5. 5
   WashThe filtrate was washed with Na2S2O5 (10% solution in water, 150 mL), NaHCO3 (sat. in water, 150 mL) and water (150 mL)
6. 6
   Dryingdried (MgSO4)
7. 7
   Concentrationconcentrated under vacuum
8. 8
   workup.STIRRINGstirred vigoursly for 1 h
9. 9
   Temperaturecooled in an ice bath for 1 h
10. 10
    Filtrationfiltered
11. 11
    Washrinsing with ice cold hexane (200 mL)

Procedure

Silver trifluoroacetate (12.3 g, 56.7 mmol) was added to a solution of isovanillin isopropyl ether (10.0 g, 51.5 mmol) in dry chloroform (120 mL) under nitrogen and the resultant slurry stirred and heated to 61° C. Iodine (14.4 g, 56.7 mmol) was then added portionwise (6 portions) over 0.6 h and the reaction allowed to reflux for a futher 6.5 h. The reaction mixture was then cooled and filtered, rinsing with chloroform (50 mL). The filtrate was washed with Na2S2O5 (10% solution in water, 150 mL), NaHCO3 (sat. in water, 150 mL) and water (150 mL) dried (MgSO4) and concentrated under vacuum. The solid residue was suspended in hexane (200 mL) and stirred vigoursly for 1 h, cooled in an ice bath for 1 h and filtered rinsing with ice cold hexane (200 mL) to give the title compound as a cream solid (15.3 g, 93%) mp 75-6° C. IR (KBr disc, cm−1) 3072, 2978, 2932, 1673, 1581, 1503, 1438, 1385, 1332, 1260, 1215, 1174, 1157, 1133, 1105, 1024, 939. 1H NMR (300 MHz, CDCl3) δ 9.77 (s, 1H,), 7.34 (s, 1H), 7.24 (s, 1H), 4.57 (septet, J=6.0 Hz, 1H), 3.86 (s, 3H), 1.31 (d, J=6.0 Hz, 6H). 13C NMR+APT (75.5 MHz, CDCl3) δ 194.7 (−), 155.5 (+), 147.9 (+), 128.2 (+), 122.2 (−), 114.1 (−), 110.8 (+), 92.4 (+), 71.3 (−), 56.4 (−), 21.77 (−). MS (70 eV) m/z (%): 320 (M+·, 43), 278 (100), 249 (17), 207 (12), 150 (40). Anal. Calcd for C11H13O3I: C, 41.27; H, 4.09; I, 39.64. Found: C, 41.06; H, 3.80; I, 39.59.

Source