Salicyl Alcohol → HCID 28945849, compound

HRID 1169452Notes

Reaction equation

HRID 1169452 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:12][CH2:13][CH2:14]Br)[CH3:11].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:10]([O:12][CH2:13][CH2:14][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])[CH3:11]

Participants

6

Reactant 4

HCID 5146Salicyl AlcoholHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl ether

Product 1

HCID 28945849HCID 28945849, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-hydroxybenzyl alcohol (2.00 g), 2-bromoethyl ethyl ether (2.7 ml), potassium carbonate (4.45 g) and DMF (20 ml) was stirred at 90° C. for 3 days. The reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with a 1 N aqueous solution of sodium hydroxide 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-ethoxyethoxy)benzyl alcohol (2.30 g) as a light yellow oily substance.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with a 1 N aqueous solution of sodium hydroxide
  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-3b670b5f086643d5a1a363da0e43d7ee
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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