Sulfuric Acid → HCID 22107235, compound

HRID 1456685Notes

Reaction equation

HRID 1456685 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH2:19](O)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].S(=O)(=O)(O)O>S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([C:16]([O:18][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])=[O:17])[CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 81931-DodecanolHCID 473472Xanthone-2-carboxylic acid

Product 1

HCID 22107235HCID 22107235, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 517045Sodium AcetateCatalyst

Procedure

A mixture of 12.01 g (50 mmol) of the above 9-oxo-9H-xanthene-2-carboxylic acid, 77.4 g (420 mmol) of n-dodecanol and 0.2 g (2 mmol) of concentrated sulfuric acid is kept at 140° C. for 6 hours. The sulfuric acid is neutralized with 0.33 g (4 mmol) of sodium acetate and the excess n-dodecancl is removed by distillation (98° C./0.1 mbar). The brown residue is taken up in isopropanol and the product which has precipitated is filtered off and dried under a high vacuum. 16.7 g(82%) of n-dodecyl 9-oxo-9H-xanthene-2-carboxylate, melting point 79°-81° C., result s a beige powder.

Workup

  1. customthe excess n-dodecancl is removed by distillation (98° C./0.1 mbar)
  2. customthe product which has precipitated
  3. filtrationis filtered off
  4. customdried under a high vacuum

Sources & evidence

ORD record
ord-0472271862e1415faf3f857ff1d47573
Source dataset
uspto-grants-1998_12
Patent number
US05844024

Reaction notes

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