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

HRID 2090790Notes

Reaction equation

HRID 2090790 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-c487d4c0302949c0b3a61ee622444496
Source dataset
uspto-grants-2013_05
Patent number
US08436207B2

Reaction notes

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