3-Methylcatechol → 5-Hydroxyindole

HRID 867853

Reaction equation

HRID 867853 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.CC1C=CC=C(O)C=1O.COC1C=CC=C(O)C=1O.CC1C=CC(C)=C(O)C=1O.I([O-])(=O)(=O)=O.[Na+].[OH:46][C:47]1[CH:55]=[CH:54][CH:53]=[C:52]2[C:48]=1[CH:49]=[CH:50][NH:51]2.[NH2:56][CH2:57][CH2:58][C:59]1[CH:66]=[CH:65][C:63]([OH:64])=[C:61]([OH:62])[CH:60]=1>>[OH:46][C:47]1[CH:55]=[CH:54][CH:53]=[C:52]2[C:48]=1[CH:49]=[CH:50][NH:51]2.[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH:64][C:63]1[CH:65]=[C:66]2[C:59]([CH:58]=[CH:57][NH:56]2)=[CH:60][CH:61]=1.[OH:62][C:61]1[CH:63]=[CH:65][CH:66]=[C:59]2[C:60]=1[NH:56][CH:57]=[CH:58]2

Participants

11

Reactant 7

HCID 3403-MethylcatecholHCID 681DopamineHCID 136223-MethoxycatecholHCID 160545-HydroxyindoleHCID 754211H-indol-4-olHCID 114691143,6-Dimethylbenzene-1,2-diolHCID 23667635Sodium periodate

Product 4

HCID 160545-HydroxyindoleHCID 754211H-indol-4-olHCID 5245086-HydroxyindoleHCID 27376517-Hydroxyindole

Procedure

Mixtures of 4-hydroxyindole (0.1-10%) and 5-hydroxyindole (0.1-10%), 6-hydroxyindole (0.1-10%), or 7-hydroxyindole (0.1-10%) will give a color range from black to light auburn. 5-Hydroxyindole (0.1-10%) was found to produce progressively darker browns and, eventually, black through the addition of 3-methylcatechol (0.1-10%), 3-methoxycatechol (0.1-10%), or 3,6-dimethylcatechol (0.1-10%) followed by oxidation by sodium periodate (15%). 4-Hydroxyindole (1%) was found to produce progressively lighter colors with increasing red highlights through the addition of dopamine (2-5%) when penetration of precursors was done at high pH (9.2). Therefore a range of colors from light brown to black can be obtained through combinations of 4-hydroxyindole, 5-hydroxyindole, 6-hydroxyindole, and 7-hydroxyindole with each other or various other dye precursors. Similar results were obtained in staining skin in that a range of shades from light to dark brown can be obtained through combinations of hydroxyindoles with various other dye precursors.

Workup

  1. customto produce progressively darker browns
  2. customto produce progressively lighter colors
  3. temperaturewith increasing red highlights

Sources & evidence

ORD record
ord-479fcc00a3ac46219fa1ab4996bf34a8
Source dataset
uspto-grants-1988_10
Patent number
US04776857

Linked notes

Loading…