4-Dodecylresorcinol → HCID 178418610, compound

HRID 4879Notes

Reaction equation

HRID 4879 reaction equation
[CH2:1]([C:13]1[CH:19]=[CH:18][C:16]([OH:17])=[CH:15][C:14]=1[OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[N:21]([C:23]1[CH:29]=[CH:28][C:26]([OH:27])=[CH:25][C:24]=1O)=O>S(=O)(=O)(O)O>[CH2:1]([C:13]1[C:14](=[O:20])[CH:15]=[C:16]2[C:18](=[N:21][C:23]3[C:29]([O:17]2)=[CH:28][C:26]([OH:27])=[CH:25][CH:24]=3)[CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 904584-DodecylresorcinolHCID 1203384-Nitrosoresorcinol

Product 1

HCID 178418610HCID 178418610, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-dodecylresorcinol (8.5 g, 30.53 mmole) (Aldrich Chemical Company) and 4-nitrosoresorcinol (5.0 g, 35.9 mmole) (Aldrich) in concentrated sulfuric acid (100 mL) is heated to 67° C. with stirring for 5 hours. The reaction mixture is allowed to cool to room temperature, poured into ice-water (1800 mL) and filtered. The resulting precipitate is washed with water until the filtrate is neutral to pH paper. This precipitate is dissolved in chloroform and the combined aqueous filtrates are back-extracted with chloroform (6×250 mL) to recover additional product. The combined chloroform layers are dried over anhydrous sodium sulfate and evaporated to a dark purple solid (2.55 g), homogenous by SiO2 -t.l.c. (45:5:1 chloroform:methanol:triethylamine) Rf =0.69. An additional 5.58 g of product is obtained by neutralization of the aqueous filtrates above with 8M KOH and extraction with chloroform (total yield=8.13 g, 68%). 1H NMR (d6 -DMSO) δ:7.57(d,1H); 7.27(s,1H); 6.79(D,1H); 6.66(s,1H); 6.23(s,1H); 4.14(c,1H); 2.46(t,2H); 1.52(c,2H); 1.23(c,18H); 0.85(c,3H).

Workup

  1. filtrationfiltered
  2. washThe resulting precipitate is washed with water until the filtrate
  3. dissolutionThis precipitate is dissolved in chloroform
  4. extractionthe combined aqueous filtrates are back-extracted with chloroform (6×250 mL)
  5. customto recover additional product
  6. dry with materialThe combined chloroform layers are dried over anhydrous sodium sulfate
  7. customevaporated to a dark purple solid (2.55 g), homogenous by SiO2 -t.l.c

Sources & evidence

ORD record
ord-0efa13a49ba14cf48bbde9a169b7b718
Source dataset
uspto-grants-1993_09
Patent number
US05242805

Reaction notes

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