Hydrochloric Acid → Methyl 9-hydroxyxanthene-9-carboxylate

HRID 750547Notes

Reaction equation

HRID 750547 reaction equation
[CH:1]1[C:14]2[CH:13]([C:15]([O:17][CH3:18])=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CC(C)([O-:22])C.[K+].O=O.Cl>O1CCCC1>[OH:22][C:13]1([C:15]([O:17][CH3:18])=[O:16])[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 699662methyl 9H-xanthene-9-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 12068826Methyl 9-hydroxyxanthene-9-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

48.05 g (0.2 mol) methyl xanthene-9-carboxylate are dissolved in 1200 mL of tetrahydrofuran and at 0° C. combined with 23.63 g (0.2 mol) of potassium tert-butoxide. Oxygen is the piped in for 2 hours at −10° C. to −5° C., then the mixture is acidified with 2 N aqueous hydrochloric acid and the majority of the solvent is distilled off. The residue remaining is extracted with ethyl acetate and water, the organic phase is extracted with aqueous Na2S2O5 solution, washed with water, and dried, and the solvent is distilled off. The product is purified by crystallization from diisopropylether and cyclohexane. Yield: 11.10 g white crystals (22% of theoretical yield)

Workup

  1. customin for 2 hours
  2. customat −10° C. to −5° C.
  3. distillationthe majority of the solvent is distilled off
  4. extractionThe residue remaining is extracted with ethyl acetate and water
  5. extractionthe organic phase is extracted with aqueous Na2S2O5 solution
  6. washwashed with water
  7. customdried
  8. distillationthe solvent is distilled off
  9. customThe product is purified by crystallization from diisopropylether and cyclohexane

Sources & evidence

ORD record
ord-d580b756b3da4b4697e1670f33459cf0
Source dataset
uspto-grants-2008_07
Patent number
US07405224B2

Reaction notes

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