Salicyl Alcohol → HCID 70023923, compound

HRID 1169444Notes

Reaction equation

HRID 1169444 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[CH2:10]([O:13][CH2:14][CH2:15]Cl)[CH2:11][CH3:12].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O.CN(C=O)C>[CH2:10]([O:13][CH2:14][CH2:15][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])[CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 5146Salicyl AlcoholHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1235061-(2-Chloroethoxy)propane

Product 1

HCID 70023923HCID 70023923, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-hydroxybenzyl alcohol (3.00 g), 2-chloroethyl propyl ether (4.0 ml), sodium iodide (4.75 g), potassium carbonate (6.68 g) and DMF (30 ml) was stirred at 90° C. for 24 hours. The reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to purification using column chromatography (ethyl acetate:hexane 1:2) to obtain 2-(2-propoxyethoxy)benzyl alcohol (2.35 g) as a yellow oily substance.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was subjected to purification

Sources & evidence

ORD record
ord-52d4f213faf1455db9f11a77c1fb0e57
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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