Hydrochloric Acid → 2-(2-Hydroxy-1-phenylethylsulfanyl)benzene-1,4-diol

HRID 31314

Reaction equation

HRID 31314 reaction equation
[SH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[C:16]1([CH:22]2[CH2:24][O:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>O>[OH:23][CH2:24][CH:22]([S:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[OH:9])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7276Styrene OxideHCID 11430Potassium CarbonateHCID 27361672-Mercaptobenzene-1,4-diol

Product 1

HCID 179785022-(2-Hydroxy-1-phenylethylsulfanyl)benzene-1,4-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2-mercaptobenzene-1,4-diol (0.5 g) and potassium carbonate (0.49 g) in water (5 ml) was added 2-phenyloxirane (0.40 ml) under argon. The mixture was stirred at room temperature for 2.5 hours and then treated with 2 M HCl and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried and evaporated. The crude product was purified by column chromatography using heptane-ethyl acetate (1:1) as an eluant. 1H NMR (400 MHz, d6-DMSO) δ: 8.94 (br s, 1H), 8.72 (br s, 1H), 7.24-7.37 (m, 5H), 6.62-6.65 (m, 2H), 6.47 (dd, 1H, J 8.6, 2.8 Hz), 4.97 (br s, 1H), 4.34 (m, 1H), 3.72 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water and brine
  3. customdried
  4. customevaporated
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-64fdd82e7fb34dfcb404b245e8d54464
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Linked notes

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