Sulfuric Acid → (2,2'-Binaphthalene)-1,1',6,6',7,7'-hexol, 5,5'-diisopropyl-3,3'-dimethyl-

HRID 1666029Notes

Reaction equation

HRID 1666029 reaction equation
[CH3:1][C:2]1[C:24]([C:25]2[C:26]([CH3:52])=[CH:27][C:28]3[C:38]([CH:39]([CH3:41])[CH3:40])=[C:37]([O:42]C(C)=O)[C:36]([O:46]C(C)=O)=[C:35](C=O)[C:29]=3[C:30]=2[O:31]C(C)=O)=[C:23]([O:53]C(C)=O)[C:5]2=[C:6](C=O)[C:7]([O:17]C(C)=O)=[C:8]([O:13]C(C)=O)[C:9]([CH:10]([CH3:12])[CH3:11])=[C:4]2[CH:3]=1.OS(O)(=O)=O>[OH-].[Na+]>[CH3:52][C:26]1[C:25]([C:24]2[C:2]([CH3:1])=[CH:3][C:4]3[C:9]([CH:10]([CH3:11])[CH3:12])=[C:8]([OH:13])[C:7]([OH:17])=[CH:6][C:5]=3[C:23]=2[OH:53])=[C:30]([OH:31])[C:29]2=[CH:35][C:36]([OH:46])=[C:37]([OH:42])[C:38]([CH:39]([CH3:40])[CH3:41])=[C:28]2[CH:27]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 35450Gossypol hexaacetate

Product 1

HCID 454878(2,2'-Binaphthalene)-1,1',6,6',7,7'-hexol, 5,5'-diisopropyl-3,3'-dimethyl-Yield 95%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

More specifically, the gossypol acetic acid 1 (5 g, 8.65 mmol) in 50 ml of 40% NaOH was heated under nitrogen at 90° C. for 3.5 hours in the dark. The reaction mixture was cooled and poured slowly onto ice (300 ml) and concentrated H2SO4 (35 ml) mixture to form white precipitation. The precipitation was filtered, washed with water and dried to afford apogossypol (3.8 g, 95%) as a white solid. 1H NMR (CDCl3 δ 7.61 (s, 2H), 7.50 (s, 2H), 5.93 (s, 2H), 5.27 (s, 2H), 5.13 (s, 2H), 3.88 (m, 2H), 2.12 (s, 6H), 1.55 (d, J=5.5 Hz, 12H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customto form white
  3. customprecipitation
  4. customThe precipitation
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-be0e14856da841418d83d3860b5071ef
Source dataset
uspto-grants-2011_10
Patent number
US08039668B2

Reaction notes

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