Synthesis of 4-iodoanisole

Preparation of 4-iodoanisole

Preparation of 4-iodoanisole

Preparation of 4-iodoanisole

10 ml of 30% hydrogen peroxide are added in small portions during 20 min to a mixture of 5.93 g of anisole, 6.97 g of powdered iodine, 30 ml of 95% ethanol, and 10 ml of conc. sulfuric acid. The mixture is warmed and stirred vigorously after each addition. When about 5 ml of the hydrogen peroxide solution have been added a violent reaction sets in, which is allowed to moderate before any further addition. On cooling of the solution and dilution with water a dark oil separates, which is collected in ether which is then washed with sodium thiosulfate solution and water and dried over calcium chloride. The ether is removed, whereafter the residue crystallizes in a refrigerator yielding 11.2 g, of crude 4-iodoanisole m.p. 49°. After recrystallization from 90% ethanol 4-iodoanisole m.p. 50° C, overall yield 80%.

Aust. J. Sci. Res., 2 A, 595 (1949).

Preparation of 4-iodoanisole

Preparation of 4-iodoanisole

20 ml of anisole are heated to 100° C with 4.4 g of silver trifluoroacetate and then cooled to room temperature. Adding 5.1 g of finely powdered iodine causes silver iodide to be precipitated. The mixture is heated at 100° C for 15 min, then cooled, filtered, and distilled. The product, b.p. 235-237°, is obtained in 75% yield.

J. Chem. Soc, 1952, 1000.

IUPAC Name

1-iodo-4-methoxybenzene

InChI

InChI=1S/C7H7IO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3

InChI Key

SYSZENVIJHPFNL-UHFFFAOYSA-N

Canonical SMILES

COC1=CC=C(C=C1)I

MeSH Synonyms

4-iodoanisole, Izoform

Depositor-Supplied Synonyms

4-Iodoanisole, p-Iodoanisole, 696-62-8, 1-Iodo-4-methoxybenzene, 4-Methoxyiodobenzene, Benzene, 1-iodo-4-methoxy-, Isoform, p-Methoxyiodobenzene, 4-iodo-anisole, Anisole, p-iodo-, 1-iodo-4-methoxy-Benzene, 4-Iodomethoxybenzene, p-Iodophenyl methyl ether, 4-Iodophenyl methyl ether, p-Methoxyphenyl iodide, SYSZENVIJHPFNL-UHFFFAOYSA-N, RARECHEM FH 10 0029, NSC 60727, ST51041390, AURORA KA-7366, p-Iodoanisol, 4-Iodoanisol, 4-iodo-anisol, para-iodo anisole, p-Iodomethoxybenzene, Anisole, 4-iodo-, ZINC00391101, p-methoxy iodobenzene, 4-methoxy iodobenzene, PubChem3911, 4-Methoxyphenyl iodide, p-methoxy-phenyl-iodide, 4-IODOAISOLE, 4-iodo-1-methoxybenzene, 4-methoxy-1-iodobenzene, AC1L2CET, AC1Q4PJS, para-methoxy iodo-benzene, ACMC-1AZ6S, AC1Q4CX9, I7608_ALDRICH, Anisole, p-iodo- (8CI), SCHEMBL24567, 1-iodo-4-(methyloxy)benzene, KSC354K7N, 696-62-8 4-Iodoanisole, CTK2F4576, MolPort-000-156-437, ZINC391101, ACT00265, NSC60727, STR08687, EINECS 211-798-7, ANW-35742, AR-1L1001, NSC-60727, WT1399, AKOS000120028, AS02208, AS04204, MCULE-1365359457, RP17556, RTC-040229, TF10516, TRA0044441, AC-13968, AJ-21028, AK-44747, AN-47274, BR-44747, CJ-03466, KB-39315, OR011655, OR145809, SC-06341, ZB011947, AB1003788, DB-024218, ST2418425, TC-040229, TL8004894, AM20041028, FT-0618779, I0378, 2119-EP1441224A2, 2119-EP2269610A2, 2119-EP2272517A1, 2119-EP2277876A1, 2119-EP2280011A1, 2119-EP2281815A1, 2119-EP2289510A1, 2119-EP2289892A1, 2119-EP2289893A1, 2119-EP2292614A1, 2119-EP2295433A2, 2119-EP2298742A1, 2119-EP2301533A1, 2119-EP2301933A1, 2119-EP2305640A2, 2119-EP2311464A1, 2119-EP2311801A1, 2119-EP2311802A1, 2119-EP2311803A1, 2119-EP2311818A1, 2119-EP2311823A1, 2119-EP2311827A1, 2119-EP2311832A1, 2119-EP2311833A1, 2119-EP2314574A1, 2119-EP2314576A1, 2119-EP2316457A1, 2119-EP2316458A1, 2119-EP2316825A1, 2119-EP2316826A1, 2119-EP2316827A1, 2119-EP2316828A1, 2119-EP2371814A1, 2119-EP2374792A1, A19934, S-1482, 4-Iodophenyl methyl ether; 4-Methoxyiodobenzene, S01-0136, W-104609, 3B3-020069, InChI=1/C7H7IO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H

Removed Synonyms

CID69676, 95428-88-9

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