Water → Methyl 4-(chloromethyl)benzoate

HRID 744176Notes

Reaction equation

HRID 744176 reaction equation
CN([CH:4]=[O:5])C.N[C@H](C(O)=O)[CH2:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=CC=C2)=[CH:11][CH:10]=1.[Cl:22]C1C=CC=C(Cl)C=1[O-].[Na+].[OH2:32]>C(Cl)Cl>[Cl:22][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:5][CH3:4])=[O:32])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 1859152-NaphthylalanineHCID 23663679Sodium 2,6-dichlorophenolate

Product 1

HCID 36664Methyl 4-(chloromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a mixture of 100 g of the product prepared as described in step (a)in 500 mL of dry DMF and 81.1 g (0.54168 moles) of Nal and 150 g (0.8108 moles, 1.5 eg) of sodium 2,6-dichlorophenoxide at room temperature overnight. Add water to the so-formed formed reaction mixture to produce a precipitated solid. Add CH2Cl2 to dissolve the precipitated solid. Wash the CH2Cl2 layers successively with four volumes of a 5% aqueous NaOH solution, water and brine. Separate and dry the organic layer over Na2SO4. Remove the solvent under reduced pressure to produce 164.5 g (97.6% of theory) of the title compound. The 200 MHzNMR spectrum is consistent with the proposed ester structure ##STR121##

Workup

  1. customprepared
  2. customreaction mixture
  3. customto produce a precipitated solid
  4. washWash the CH2Cl2 layers successively with four volumes of a 5% aqueous NaOH solution, water and brine
  5. customSeparate
  6. dry with materialdry the organic layer over Na2SO4
  7. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-c501f549e330405da5d699a2f96559a5
Source dataset
uspto-grants-1996_09
Patent number
US05559133

Reaction notes

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