Hydrochloric Acid → (E)-S-phenyl 3-(4-hydroxy-3,5-dimethylstyryl)benzothioate

HRID 2368869Notes

Reaction equation

HRID 2368869 reaction equation
COC[O:4][C:5]1[C:27]([CH3:28])=[CH:26][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=2)[C:14](=[O:22])[S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][C:6]=1[CH3:29].Cl>CC(O)C.C1COCC1>[OH:4][C:5]1[C:27]([CH3:28])=[CH:26][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=2)[C:14](=[O:22])[S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][C:6]=1[CH3:29]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86672878(E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate

Product 1

HCID 44472868(E)-S-phenyl 3-(4-hydroxy-3,5-dimethylstyryl)benzothioate

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate (80 mg, 0.198 mmol) in i-PrOH and THF (½ mL) was added 0.5 mL of concentrated HCl. The reaction mixture was stirred overnight (about 18 hours). After removal of solvent under reduced pressure, the residue was dissolved in EtOAc. The solution was washed with brine and dried with Na2SO4. The solution was filtered and concentrated. The compound was purified by column chromatography (9:1 Hexane:EtOAc) to afford (E)-S-phenyl 3-(4-hydroxy-3,5-dimethylstyryl)-benzothioate in quantitative yield. Azo-linked compounds of Formula I are prepared following usual syntheses for preparing aromatic or heteroaromatic azo compounds. A typical scheme is shown in Scheme 3.

Workup

  1. customAfter removal of solvent under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe solution was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customThe compound was purified by column chromatography (9:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-50e3cb7fcd494b169b23484252a2f418
Source dataset
uspto-grants-2014_04
Patent number
US08703815B2

Reaction notes

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