Phenol → (2-Chloro-1-methoxyethoxy)benzene

HRID 614013

Reaction equation

HRID 614013 reaction equation
[CH3:1][O:2][CH:3]=[CH2:4].[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:12]OC(C)(C)C>O1CCCC1>[CH3:1][O:2][CH:3]([O:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:4][Cl:12]

Participants

5

Reactant 3

HCID 996PhenolHCID 7861Methyl vinyl etherHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 21329867(2-Chloro-1-methoxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At -20° C., 10 parts by weight of vinyl methyl ether is added all at once to 4.5 parts by weight of phenol in 50 parts by weight of tetrahydrofuran. Over a period of 30 minutes and at -20° C., 10 parts of tert.-butyl hypochlorite (Org. Synthesis, Coll. Vol. IV, 125, John Wiley & Sons, Inc., New York/London, 1963) is dripped into this mixture. The resultant mixture is allowed to come to room temperature. After stirring for 2 hours at room temperature, the solvent is removed, and distillation gives 5 parts by weight of 1-methoxy-1-phenoxy-2-chloroethane, b.p. 89°-91° C./4mm Hg.

Workup

  1. customat -20° C.
  2. customto come to room temperature
  3. customthe solvent is removed
  4. distillationdistillation

Sources & evidence

ORD record
ord-ca8c34fdea904e07a88323fd615b038e
Source dataset
uspto-grants-1979_03
Patent number
US04143064

Linked notes

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