Diethyl Ether → HCID 15058653, compound

HRID 594319Notes

Reaction equation

HRID 594319 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[F:19][CH2:20][CH2:21]I.CCOCC>CN(C=O)C.O>[F:19][CH2:20][CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-

Product 1

HCID 15058653HCID 15058653, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of commercially available ethyl 4-hydroxybenzoate (2.500 g; 15.04 mmol), K2CO3 (4.158 g; 30.08 mmol), and 1-fluoro-2-iodoethane (2.617 g; 15.04 mmol) in anh. DMF (30 ml) was heated to 70° C., under nitrogen, for 2.5 h. After cooling to rt, Et2O (100 ml) and water (50 ml) were added. The separated organic layer was further washed with water (2×50 ml), dried over anh. MgSO4, filtered, concentrated to dryness under reduced pressure, and the residue was further dried under HV affording ethyl 4-(2-fluoroethoxy)benzoate as a colorless solid. LC-MS (conditions D): tR=0.96 min.; no ionisation.

Workup

  1. temperatureAfter cooling to rt
  2. washThe separated organic layer was further washed with water (2×50 ml)
  3. dry with materialdried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customthe residue was further dried under HV

Sources & evidence

ORD record
ord-3b07e5819794451c90835f45d208c43a
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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