4-Chloro-3-methylphenol → HCID 22467254, compound

HRID 337618Notes

Reaction equation

HRID 337618 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].C([O-])([O-])=O.[K+].[K+].Br[CH2:17][CH2:18][O:19][CH3:20]>CN(C=O)C.O.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH2:18][O:19][CH3:20])=[CH:4][C:3]=1[CH3:9]

Participants

7

Reactant 3

HCID 17324-Chloro-3-methylphenolHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 22467254HCID 22467254, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-chloro-3-methylphenol (1 eq.) in DMF (0.7 M) was added K2CO3 (1.2 eq.). The mixture was stirred at 50° C. for 5 min before 1-bromo-2-methoxyethane (1.5 eq.) was added. After 2 h at 70° C., the reaction mixture was cooled down to RT and then diluted with water and ether. The organic phase was separated and washed sequentially with 2 N aq. NaOH, water and brine. The organic extract was dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the title compound as a yellowish oil.

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. washwashed sequentially with 2 N aq. NaOH, water and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-ce8696ec85d046e4b4bc07a5a4c1936d
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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