Sulfuric Acid → HCID 59850855, compound

HRID 2373111Notes

Reaction equation

HRID 2373111 reaction equation
[CH2:1]([O:5][C:6]1[CH:21]=[CH:20][C:9]([O:10][C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O>C(OC(=O)C)(=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:10][C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13](=[O:15])[C:20]=2[CH:21]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 69286253HCID 69286253, compound

Product 1

HCID 59850855HCID 59850855, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Finally, 2-butoxyxanthen-9-one (S-14) was synthesized. A stirred suspension under argon of 2-(4-butoxyphenoxy)benzoic acid (8.2 g, 29 mmol) in acetic anhydride (50 mL) was treated with 2.8 g (29 mmol) of concentrated sulfuric acid, and then held at 80° C. for 3 h. The mixture was cooled to ambient, and then poured onto 500 g of ice. The precipitated crude product was collected, washed with water, and air dried. The product was purified by column chromatography followed by recrystallization from 50% aqueous ethanol. A white powder was obtained. 1H NMR (CDCl3): δ 1.00 (t, 3H), 1.5 (m, 2H), 1.85 (m, 2H), 4.08 (t, 2H), 7.3-7.5 (m, 4H), 7.7 (m, 2H), 8.36 (d, 1H).

Workup

  1. temperatureThe mixture was cooled to ambient, and
  2. customThe precipitated crude product
  3. customwas collected
  4. washwashed with water, and air
  5. customdried
  6. customThe product was purified by column chromatography
  7. customfollowed by recrystallization from 50% aqueous ethanol
  8. customA white powder was obtained

Sources & evidence

ORD record
ord-f3ebc37c1fde41a3a684bcc72fb02e82
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

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