Acetic Anhydride → HCID 15020963, compound

HRID 362587Notes

Reaction equation

HRID 362587 reaction equation
[OH:1][CH2:2][CH:3]1[C:15]2[C:10](=[C:11]3[CH:23]=[CH:22][CH:21]=[CH:20][C:12]3=[C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]3=2)[C:9]2[C:4]1=[C:5]1[CH:31]=[CH:30][CH:29]=[CH:28][C:6]1=[C:7]1[CH:27]=[CH:26][CH:25]=[CH:24][C:8]1=2.[C:32](OC(=O)C)(=[O:34])[CH3:33]>OS(O)(=O)=O>[C:32]([O:1][CH2:2][CH:3]1[C:15]2[C:10](=[C:11]3[CH:23]=[CH:22][CH:21]=[CH:20][C:12]3=[C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]3=2)[C:9]2[C:4]1=[C:5]1[CH:31]=[CH:30][CH:29]=[CH:28][C:6]1=[C:7]1[CH:27]=[CH:26][CH:25]=[CH:24][C:8]1=2)(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10927385HCID 10927385, compound

Product 1

HCID 15020963HCID 15020963, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

17-Hydroxymethyltetrabenzo(a,c,g,i)fluorene (0.207 g, 0.522 mmol) was dissolved in acetic anhydride (4 ml). To this solution was added 2 drops of H2SO4 (2M). The reaction mixture was stirred for 1 h. Compound (35) was obtained as a yellow solid which was washed with water (80 ml) and dried to constant weight over P2O5 in a vacuum desiccator (183.8 mg, 80%); m.p. 209°-210°, (Found: C, 87.0; H, 5.08 C32H22O2 requires: C, 87.7; H, 5.02%); t.l.c. Rf (A) 0.32, Rf (F) 0.22; νmax (CH2Cl2) 3060 (CH stretching, aromatic), 1740 (CO, ester), 1610, 1500 (aromatic rings), 1230, 1045 (CO, stretching) cm-1 ; λmax 380 (17885), 368 (19345), 302 (45260), 290 (36865), 254 (72271) nm; δH (CDCl3, 80 MHz), 8.83-8.57 (6H, m, aromatic), 8.29-8.17 (2H, m, aromatic), 7.78-7.54 (8H, m, aromatic), 5.12 (1H, t, 3J=5.5 Hz, CH), 4.60 (2H, d, 3J=5.5 Hz, CH2), 1.84 (3H, s, CH3); δC (CDCl3, 50 MHz) 170.7 (CO, ester), 141.8, 137.0, 131.5, 130.4, 128.6, 128.0 (quaternary aromatic C's), 127.4, 126.8, 126.1, 126.0, 125.0, 124.9, 123.5, 123.3 (aromatic CH's), 67.9 (CH2), 47.1 (CH), 20.7 (CH3); m/z (EI) 438 (M+), 378, 364.

Sources & evidence

ORD record
ord-6f52f06be86b4ebba731bb0bde7551f7
Source dataset
uspto-grants-1999_02
Patent number
US05869605

Reaction notes

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