Dibenzothiophene → 4-Hydroxydibenzothiophene

HRID 1293452Notes

Reaction equation

HRID 1293452 reaction equation
C([Li])CCC.[CH:6]1[C:14]2[C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[S:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.C1C[O:22]CC1>>[OH:22][C:9]1[C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[C:14]=2[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 3023DibenzothiopheneHCID 8028TetrahydrofuranHCID 178418339Butyllithium

Product 1

HCID 1548734-Hydroxydibenzothiophene

Procedure

n-Butyllithium (26.25 g, 406 mmols, 175 ml of 2.4M solution in hexane) was added to a stirred solution of dibenzothiophene (25 g, 135.7 mole) in dry THF (200 ml) at 0° C. over a period of 1 hr under dry N2 atmosphere. This reaction mixture was stirred overnight at room temperature and dry oxygen gas was bubbled into the reaction mixture over 5 hrs. This reaction mixture was poured slowly over cold 1N HCl (500 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×500 ml). Organic layers were mixed together and concentrated to dryness to get crude product (32 g). The crude product was purified by silica gel column chromatography.

Workup

  1. customdry oxygen gas was bubbled into the reaction mixture over 5 hrs
  2. additionThis reaction mixture was poured slowly over cold 1N HCl (500 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×500 ml)
  5. additionOrganic layers were mixed together
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4919fd54f84b45adaad16f39f848a0bf
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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