Diethyl Ether → HCID 23210564, compound

HRID 594273Notes

Reaction equation

HRID 594273 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=[O:5].I[CH2:12][CH3:13].C([O-])([O-])=O.[K+].[K+].CCOCC>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:12][CH3:13])[C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 5283932-Chloro-6-hydroxybenzaldehyde

Product 1

HCID 23210564HCID 23210564, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of commercially available 2-chloro-6-hydroxybenzaldehyde (2.000 g; 12.80 mmol), iodoethane (3.985 g; 25.50 mmol), and K2CO3 (2.119 g; 15.30 mmol) in anh. DMF (35 ml) was heated to 80° C., under nitrogen, for 1 h. Et2O was added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 2-chloro-6-ethoxybenzaldehyde as a yellow solid. LC-MS (conditions A): tR=0.75 min.; [M+H]+: 185.39 g/mol.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b81f710245624ba7a267a068a99bbc89
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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