Sulfuric Acid → HCID 59850854, compound

HRID 2373109Notes

Reaction equation

HRID 2373109 reaction equation
[C:1]([C:6]1[CH:21]=[C:20]([C:22]([CH2:25][CH3:26])([CH3:24])[CH3:23])[CH:19]=[CH:18][C:7]=1[O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2].C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>>[C:22]([C:20]1[CH:21]=[C:6]([C:1]([CH2:4][CH3:5])([CH3:3])[CH3:2])[C:7]2[O:8][C:9]3[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:11](=[O:12])[C:18]=2[CH:19]=1)([CH2:25][CH3:26])([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 69286285HCID 69286285, compound

Product 1

HCID 59850854HCID 59850854, compound

Procedure

Finally, 2,4-di-(tert-amyl)xanthen-9-one (S-13) was prepared. To a suspension of 2,4-di-(tert-amyl)phenoxybenzoic acid (4.8 g, 13.6 mmol) in acetic anhydride (27.7 g, 272 mmol) was added dropwise sulfuric acid (1.33 g, 13.6 mmol), and then the mixture was held at 80° C. for 3 h. The reaction mixture was cooled to ambient and poured into 100 mL of ice water. The aqueous phase was extracted twice with dichloromethane, and the combined organic extracts were washed with water and then with brine. The solution was dried (Na2SO4) and concentrated deposit a brown solid. The product was purified by column chromatography to provide 3.5 g (76% of theory) of a white solid. 1H NMR (CDCl3): δ 0.75 (t, 6H), 1.3 (s, 6H), 1.4 (s, 6H), 1.65 (q, 2H), 1.80 (q, 2H), 3.85 (s, 3H), 6.80 (d, 2H), 7.15 (m, 2H), 7.35 (br s, 1H), 7.45 (t, 1H), 8.2 (d, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient and
  2. extractionThe aqueous phase was extracted twice with dichloromethane
  3. washthe combined organic extracts were washed with water
  4. dry with materialThe solution was dried (Na2SO4)
  5. concentrationconcentrated deposit a brown solid
  6. customThe product was purified by column chromatography
  7. customto provide 3.5 g (76% of theory) of a white solid

Sources & evidence

ORD record
ord-cb7cfeec900e42f39aa8d8ef165d0e2a
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

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