1-Octanol → HCID 140543966, compound

HRID 576448Notes

Reaction equation

HRID 576448 reaction equation
[OH:1][C:2]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([OH:20])=[C:12]2[C:3]=1[C:4](=[O:27])[C:5]1[CH:6]=[C:7]3[C:25](=[O:26])[O:24][C:22](=[O:23])[C:8]3=[CH:9][C:10]=1[C:11]2=[O:21].[CH2:28]([OH:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].S(=O)(=O)(O)O.O>CO>[CH2:28]([O:36][C:22]([C:8]1[C:7]([C:25]([O:24][CH2:18][CH2:19][CH2:2][CH2:3][CH2:4][CH2:5][CH2:10][CH3:9])=[O:26])=[CH:6][C:5]2[C:4](=[O:27])[C:3]3[C:12](=[C:13]([OH:20])[C:14]4[C:19]([C:2]=3[OH:1])=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:11](=[O:21])[C:10]=2[CH:9]=1)=[O:23])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 962WaterHCID 1118Sulfuric AcidHCID 140543972HCID 140543972, compound

Product 1

HCID 140543966HCID 140543966, compoundYield 164.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.89 g (5.2 mmoles) of 6,11-dihydroxy-naphthacene-5,12-dione-2,3-dicarboxylic acid anhydride (product of example 9), 6.77 g (52 mmoles) of 1-octanol, and 0.2 g (2.08 mmoles) of 96% sulfuric acid are refluxed for 3 h with azeotropic removal of the reaction water. The mixture is kept at 25° for 18 h, then stirred with methanol and filtered. The precipitate is washed with water and dried in vacuo to give 2.58 g (81%) of red crystals, m.p. 95-96°.

Workup

  1. filtrationfiltered
  2. washThe precipitate is washed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b7934c4070b4408eb5745fc16dbf504f
Source dataset
uspto-grants-2015_05
Patent number
US09039946B2

Reaction notes

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