2-((4-Hydroxyphenyl)amino)-5-methoxybenzenemethanol → 4-(2-Hydroxymethyl-4-methoxyphenylimino)-2,5-cyclohexadien-1-one

HRID 2413278Notes

Reaction equation

HRID 2413278 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[CH2:17][OH:18])=[CH:4][CH:3]=1.I([O-])(=O)(=O)=O.[Na+]>C(Cl)Cl>[OH:18][CH2:17][C:10]1[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=1[N:8]=[C:5]1[CH:6]=[CH:7][C:2](=[O:1])[CH:3]=[CH:4]1

Participants

4

Reactant 2

HCID 1245222-((4-Hydroxyphenyl)amino)-5-methoxybenzenemethanolHCID 23667635Sodium periodate

Product 1

HCID 133714824-(2-Hydroxymethyl-4-methoxyphenylimino)-2,5-cyclohexadien-1-oneYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3.7 g of 2-(4-hydroxyphenylamino)-5- methoxybenzenemethanol (Example 1c) in 300 ml of methylene dichloride was added 32 g of silica treated sodium metaperiodate. The reaction mixture was stirred for two hours at room temperature, then filtered and washed with water and dried over anhydrous sodium sulfate. The solution was concentrated and the residue triturated with hexane to give 1.1 g of 4-(2-hydroxymethyl-4-methoxyphenylimino)-2,5-cyclohexadien-1-one, m.p. 87°-89° C.

Workup

  1. additionwas added 32 g of silica
  2. filtrationfiltered
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solution was concentrated
  6. customthe residue triturated with hexane

Sources & evidence

ORD record
ord-3db69936d94c440faabd447e3e91690f
Source dataset
uspto-grants-1985_01
Patent number
US04496590

Reaction notes

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