Phenol → M-Cresol

HRID 574052Notes

Reaction equation

HRID 574052 reaction equation
[ClH:1].[OH-].[Na+:3].[C:4]1([OH:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[C:12]([OH:24])(=[O:23])[CH2:13][C:14]([CH2:19][C:20]([OH:22])=[O:21])([C:16]([OH:18])=[O:17])[OH:15]>C([O-])(=O)C.[Zn+2].C([O-])(=O)C.OCC(CO)O>[C:4]1([OH:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:13]1[C:12]([OH:24])=[CH:4][CH:20]=[CH:19][C:14]=1[CH3:16].[Na+:3].[Cl-:1].[OH2:15].[C:12]([OH:24])(=[O:23])[CH2:13][C:14]([CH2:19][C:20]([OH:22])=[O:21])([C:16]([OH:18])=[O:17])[OH:15]

Participants

9

Reactant 3

HCID 996PhenolHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 22237896HCID 22237896, compound2×

Product 4

HCID 342M-CresolHCID 996PhenolHCID 5234Sodium ChlorideHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalystHCID 753GlycerolSolvent

Procedure

An aqueous solution (Stock solution I) of phenol, m-cresol, glycerol and NaCl was prepared together with an aqueous solution (Stock solution II) of LysB29Nε-hexadecandioyl-γ-Glu desB30 human insulin. An aqueous solution (Stock solution III) of citrate (citric acid, monohydrate) was prepared and pH was adjusted to 7.4 using diluted HCl/NaOH. A fraction of Stock solution I was mixed with variable amounts of Stock solution III and a fraction of Stock solution II was added and pH was adjusted to about 7.5. An aqueous 10 mM zinc acetate solution was added in six equal portions, pH was adjusted to 7.4 using diluted HCl/NaOH and the solution was filtered through a 0.22 μm sterile filter.

Workup

  1. filtrationthe solution was filtered through a 0.22 μm sterile filter

Sources & evidence

ORD record
ord-06313db79fb4422c9b1faa1c40d339ad
Source dataset
uspto-grants-2015_05
Patent number
US09034818B2

Reaction notes

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