Acetic Anhydride → HCID 15020961, compound

HRID 278628Notes

Reaction equation

HRID 278628 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 (CH2C2) 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-45403aec19954896b5eb32ee117676cf
Source dataset
uspto-grants-2002_03
Patent number
US06359113B1

Reaction notes

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