Potassium Hydroxide → HCID 9905718, compound

HRID 611738Notes

Reaction equation

HRID 611738 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:20]3[C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[S:17][C:16]=3[CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[K+]>O1CCCC1.CO>[C:12]1([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:25])=[O:2])=[CH:7][CH:8]=2)[C:20]2[C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[S:17][C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 9906319HCID 9906319, compound

Product 1

HCID 9905718HCID 9905718, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(dibenzothiophen-1-yl)-phenoxy]-acetic acid methyl ester (0.911 g, 2.61 mmol) in tetrahydrofuran (15 mL) and methanol (5 mL) was added an aqueous solution of potassium hydroxide (1N, 3.10 mL, 3.10 mmol, 1.2 eq) dropwise at room temperature. After stirring 1 hour at room temperature the solvents were removed. The residue was dissolved in water (125 mL) and was acidified with 10% aqueous hydrochloric acid. The water was removed and the solid was triturated in petroleum ether. Recrystallization from boiling acetic acid with hot filtration to give the title compound as a white crystalline solid (0.458 g, 52%): mp 169.5-170.5° C.; NMR (CDCl3): δ 7.88-7.81 (m, 2H), 7.48-7.39 (m, 3H), 7.37-7.32 (m, 1H), 7.26-7.17 (m, 2H), 7.13-7.08 (m, 3H), 4.83 (s, 2H); MS (El): [M+] 334; Anal. Calc. for C20H14O3S: C, 71.84, H, 4.22, N, 0.00. Found: C, 71.04, H, 3.90, N, 0.09.

Workup

  1. customwere removed
  2. dissolutionThe residue was dissolved in water (125 mL)
  3. customThe water was removed
  4. customthe solid was triturated in petroleum ether
  5. customRecrystallization
  6. filtrationwith hot filtration

Sources & evidence

ORD record
ord-4fca94df92d84ae49922764b676e8835
Source dataset
uspto-grants-1999_12
Patent number
US06001867

Reaction notes

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