Iodine → HCID 11579991, compound

HRID 1508545Notes

Reaction equation

HRID 1508545 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[I:12]I>CO.S([O-])([O-])(=O)=O.[Ag+2]>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[C:9]([I:12])[CH:10]=1

Participants

5

Reactant 2

HCID 807IodineHCID 824523-(4-Hydroxyphenyl)propanol

Product 1

HCID 11579991HCID 11579991, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(3-hydroxypropyl)phenol (2.00 g, 13.14 mmol) in MeOH (10 ml) under nitrogen at RT was added silver sulfate (4.10 g, 13.14 mmol) followed by iodine (3.34 g, 13.14 mmol). The resulting mixture was stirred at room temperature for 30 minutes, then, the solids were filtered washing with MeOH. The filtrate was concentrated and purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 7.51 (d, J=2.1 Hz, 1H); 7.02-6.97 (m, 1H); 6.73 (d, J=8.2 Hz, 1H); 3.53 (t, J=6.5 Hz, 2H); 2.59-2.51 (m, 2H); 1.80-1.71 (m, 2H).

Workup

  1. filtrationthe solids were filtered
  2. washwashing with MeOH
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash column chromatography on silica gel
  5. washeluting with EtOAc in hexanes

Sources & evidence

ORD record
ord-9d7eed380fa94913ba9bb672a72b326d
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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