Iodine → Methyl 5-iodo-6-methoxynaphthalene-1-carboxylate

HRID 1074434Notes

Reaction equation

HRID 1074434 reaction equation
[I:1]I.I(O)(=O)=O.[CH3:7][O:8][C:9]([C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)=[O:10].S(=O)(O)[O-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.O>[CH3:7][O:8][C:9]([C:11]1[C:20]2[C:15](=[C:16]([I:1])[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)=[O:10]

Participants

8

Reactant 4

HCID 807IodineHCID 24345Iodic acidHCID 10921906Methyl 6-methoxy-1-naphthoateHCID 23665763Sodium Bisulfite

Product 1

HCID 13672312Methyl 5-iodo-6-methoxynaphthalene-1-carboxylate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

Iodine (7.08 g) and iodic acid (2.78 g) were added to a stirred solution of 6-methoxy-1-naphthalenecarboxylic acid methyl ester [15 g, 69.4 mmoles, described by C. C. Price et al., J. Amer. Chem. Soc., 69, 2261 (1947)] in 80% acetic acid (110 ml) and 98% sulfuric acid (0.97 ml). The solution was heated at 50° C. for 5 hr, cooled and poured into water (100 ml). After the addition of sodium bisulfite to destroy the unreacted iodine, the precipitate was collected, washed with water and recrystallized from ethanol to afford the title compound; mp 98°-99° C.; NMR (CDCl3) δ 3.95 (s, 3H), 4.00 (s, 3H), 8.00 (m, 5H).

Workup

  1. temperaturecooled
  2. customto destroy the unreacted iodine
  3. customthe precipitate was collected
  4. washwashed with water
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7292ad109272446a93e4d2aad7b0358c
Source dataset
uspto-grants-1983_07
Patent number
US04391825

Reaction notes

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