Acetic Acid → HCID 15020960, compound

HRID 362585Notes

Reaction equation

HRID 362585 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C(C[CH:15]1[C:27]2[C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[C:24]3[CH:32]=[CH:33][CH:34]=[CH:35][C:23]=3[C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)(O)=O.[C:36](O)(=[O:38])C.O>ClCCl>[OH:38][CH2:36][CH:22]1[C:27]2[C:26]3[CH:25]=[CH:31][CH:30]=[CH:29][C:28]=3[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]=2[C:35]2[C:23]1=[CH:24][CH:32]=[CH:33][CH:34]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 22627888HCID 22627888, compound

Product 1

HCID 15020960HCID 15020960, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisobutylaluminum hydride (4.6 ml, 4.62 mmol; 1M in CH2Cl2) was added at -65° C. to a solution of 13-carboxymethyl-dibenzo(a,c)fluorene (0.5 g, 1.54 mmol) in dichloromethane (10 ml). The reaction mixture was stirred for 3 h and the temperature maintained between -50° C. and -40° C. A white precipitate was obtained. The reaction mixture was treated with a mixture of acetic acid and water (1:1; 30 ml) and extracted with dichloromethane (3×60 ml). The organic layer was washed with saturated bicarbonate (50 ml), water (30 ml) and dried over MgSO4. The solvent was removed in vacuo to afford a crude solid. This crude solid was purified by flash chromatography using chloroform as the eluent. Compound (21) was obtained as a white solid which was washed with petrol (0.217 g, 48%); m.p. 167°-168° C.; (Found: C, 89.0; H, 5.39; C22H16O requires: C, 89.2; H, 5.41%); t.l.c. Rf (D) 0.26; Rf (E) 0.64; νmax (CH2Cl2) 3610 (free OH), 3490 (H bonded OH), 3060 (CH stretching), 2940, 2890 (CH stretching, alkyl), 1610, 1600, 1580 (aromatic rings) cm-1 ; λmax 366 (888), 338 (12728), 322 (14504), 266 (27232), 246 (31968) nm; δH (CDCl3, 200 MHz), 8.88-8.68 (3H, m, aromatic), 8.38 (1H, d, 3J=7.9 Hz, aromatic), 8.14-8.08 (1H, m, aromatic), 7.81-7.33 (7H, m, aromatic), 4.45 (2H, m, HaCH2 and Hc), 3.85 (1H, m, Hb, CH2), 1.64 (1H, S, OH), δC (CDCl3, 50 MHz), 146.7, 142.5, 139.4, 134.9, 130.9, 130.1, 128.7 (quaternary aromatic C's), 127.5, 126.8, 126.1, 125.9, 125.8, 124.7, 124.2, 124.1, 123.8, 123.4, 122.9 (aromatic CH's), 65.7 (CH), 50.0 (CH); m/z (EI) 296, 265.

Workup

  1. temperaturethe temperature maintained between -50° C. and -40° C
  2. customA white precipitate was obtained
  3. extractionextracted with dichloromethane (3×60 ml)
  4. washThe organic layer was washed with saturated bicarbonate (50 ml), water (30 ml)
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customto afford a crude solid
  8. customThis crude solid was purified by flash chromatography

Sources & evidence

ORD record
ord-f598193d1e9a4552b569b53586ce26ab
Source dataset
uspto-grants-1999_02
Patent number
US05869605

Reaction notes

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