Acetic Anhydride → HCID 15020961, compound

HRID 362586Notes

Reaction equation

HRID 362586 reaction equation
[OH:1][CH2:2][CH:3]1[C:15]2[C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C:12]3[CH:20]=[CH:21][CH:22]=[CH:23][C:11]=3[C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.[C:24](OC(=O)C)(=[O:26])[CH3:25]>S(=O)(=O)(O)O>[C:24]([O:1][CH2:2][CH:3]1[C:15]2[C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C:12]3[CH:20]=[CH:21][CH:22]=[CH:23][C:11]=3[C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15020960HCID 15020960, compound

Product 1

HCID 15020961HCID 15020961, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

13-Hydroxymethyldibenzo(a,c)fluorene (215.2 mg, 0.727 mmol) was dissolved in acetic anhydride (5 ml). To this solution was added one drop of sulfuric acid (2M). The reaction mixture was stirred for 30 min. A white precipitate was obtained which was filtered and washed with water (150 ml). The solid was finally dried to constant weight over P2O5 in a vacuum desiccator to afford 13-acetoxymethyldibenzo(a,c)fluorene as a white solid, (206.3 mg, 84%); m.p. 135°-136° C.; (Found: C, 84.9; H, 5.33 C24H18O2 requires: C, 85.2; H, 5.33%; t.l.c. Rf (D) 0.57; Rf (E) 0.68; νmax (CH2Cl2) 3030 (CH stretching, aryl) 2980, 2920 (CH stretching, alkyl) 1735 (CO, ester), 1610, 1600, 1570 (aromatic rings) cm-1 ; λmax 366 (1184), 338 (25160), 322 (27528), 265 (52688), 246 (53020) nm; δH (CDCl3, 200 MHz), 8.86-8.69 (3H, m, aromatic), 9.38 (1H, d, 3J=7.9 Hz, aromatic), 8.30-8.25 (1H, m, aromatic), 7.78-7.35 (7H, m, aromatic), 5.16 (1H, dxd, 3Ja,c =4.1 Hz, 2Ja,b =10.8 Hz, Ha, CH2), 4.56 (1H, dxd, 3Jc,a =4.1 Hz, 3Jc,b =9.3 Hz, Hc), 3.76 (1H, dxd, 2Jb,a =10.8 Hz, 3Jb,c =9.3 Hz, Hb, CH2), 2.17 (3H, s, CH3); δC (CDCl3, 50 MHz) 171.0 (CO, ester), 146.7, 142.1, 138.7, 134.8 131.1, 130.1, 128.7, 128.6 (quaternary aromatic C's), 127.6, 127.0, 126.8, 126.2, 126.1, 125.7, 124.9, 124.8, 124.3, 123.4, 123.3, 122.9 (aromatic CH's), 67.3 (CH2), 46.5 (CH), 20.9 (CH3); m/z (EI) 338, 277, 265, 139, 43.

Workup

  1. customA white precipitate was obtained which
  2. filtrationwas filtered
  3. washwashed with water (150 ml)
  4. dry with materialThe solid was finally dried to constant weight over P2O5 in a vacuum desiccator

Sources & evidence

ORD record
ord-da6d291e0f7f4d4b916dfaf74e6b5ae3
Source dataset
uspto-grants-1999_02
Patent number
US05869605

Reaction notes

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