Potassium Carbonate → HCID 86725582, compound

HRID 514458

Reaction equation

HRID 514458 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([OH:8])[CH:7]=1.I[CH2:12][CH2:13][CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([O:8][CH2:12][CH2:13][CH3:14])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 3271485-Chloro-2-(hydroxymethyl)phenol

Product 1

HCID 86725582HCID 86725582, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Charge 5-chloro-2-(hydroxymethyl)phenol (997 mg, 6.29 mmol, PREPARATION 7), iodopropane (1.17 g, 6.92 mmol), K2CO3 (1.74 g, 12.58 mmol) and DMF (6 mL) to a sealed tube. The reaction mixture was heated to 100° C. overnight. It was then poured into ice-water and extracted with ethyl acetate twice, washed the organic phase with water twice, brine and dried with Na2SO4, concentrated and purified by silica gel chromatograph to give the title compound (729 mg, 58%). 1H NMR (400 MHz, CDCl3): δ 1.05 (3H, t, J=7.2 Hz), 1.79-1.88 (2H, m), 3.96 (2H, t, J=6.4 Hz), 4.64 (2H, s), 6.85 (1H, d, J=1.2 Hz), 6.91 (1H, dd, J=1.6 Hz, 8.4 Hz), 7.20 (1H, d, J=8.0 Hz).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washwashed the organic phase with water twice
  3. dry with materialbrine and dried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatograph

Sources & evidence

ORD record
ord-0d4dfb69545f4815926283b358c2a4fc
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Linked notes

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