Sulfuric Acid → HCID 22107235, compound

HRID 726770Notes

Reaction equation

HRID 726770 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.[Na]>S(=O)(=O)(O)O>[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 4

HCID 1118Sulfuric AcidHCID 81931-DodecanolHCID 473472Xanthone-2-carboxylic acidHCID 5360545Sodium

Product 1

HCID 22107235HCID 22107235, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

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 acetam and the excess n-dodecanol 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 uider a high vacuum. 16.7 g (82%) of n-dodecyl 9-oxo-9H-xanthene-2-carboxylate, melting point 79°-81° C., result as a beige powder.

Workup

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

Sources & evidence

ORD record
ord-f2802121defa4b5e906735705b9b8d1b
Source dataset
uspto-grants-1998_01
Patent number
US05710198

Reaction notes

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