Hydrochloric Acid → HCID 17959616, compound

HRID 347327Notes

Reaction equation

HRID 347327 reaction equation
Br[C:2]1[C:15]2[CH2:14][C:13]3[C:8](=[CH:9][C:10]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][C:12]=3Br)[O:7][C:6]=2[CH:5]=[C:4]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:3]=1.C([Li])CCC.[OH-:30].[K+].[OH:32]O.Cl>CCCCCC.C1COCC1.O>[OH:30][C:2]1[C:15]2[CH2:14][C:13]3[C:8](=[CH:9][C:10]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][C:12]=3[OH:32])[O:7][C:6]=2[CH:5]=[C:4]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 17959615HCID 17959615, compoundHCID 178418339Butyllithium

Product 1

HCID 17959616HCID 17959616, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

5 g (13.3 mmol) of 1,8-dibromo-3,6-di-tert-butylxanthene together with THF were placed in a reaction vessel under argon. At −50° C., 12.3 ml (30.7 mmol) of a 2.5 molar n-butyllithium solution in hexane were added. The reaction mixture was stirred for 2 hours, resulting in formation of a colorless suspension. At 0° C., 100 ml (100 mmol) of a 1 molar solution of BH3 in THF were added dropwise and the mixture was stirred overnight at 5–15° C. It was subsequently carefully hydrolyzed at 0° C. using 25 ml of water. 3 N KOH (7.4 g of KOH in 32 g of H2O) and 10.4 g of 30% strength H2O2 solution were carefully added to the reaction mixture and the resulting mixture was refluxed for 2 hours. After cooling to room temperature, it was neutralized using 18% strength hydrochloric acid. After phase separation, the organic phase was washed twice with NaCl solution, dried over Na2SO4 and evaporated to dryness. 1,8-Dihydroxy-3,6-di-tert-butylxanthene was obtained in a yield of 4.7 g (100% of theory).

Workup

  1. customresulting in formation of a colorless suspension
  2. stirringthe mixture was stirred overnight at 5–15° C
  3. customwas subsequently carefully hydrolyzed at 0° C.
  4. temperaturethe resulting mixture was refluxed for 2 hours
  5. customAfter phase separation
  6. washthe organic phase was washed twice with NaCl solution
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-678d35793d704304b8df668b80868566
Source dataset
uspto-grants-2007_02
Patent number
US07173138B2

Reaction notes

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