Benzyl Bromide → Methyl 2-(benzyloxy)-5-chlorobenzoate

HRID 231128Notes

Reaction equation

HRID 231128 reaction equation
[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Product 1

HCID 13704267Methyl 2-(benzyloxy)-5-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 5-chlorosalicylate (5.58 g, 0.03 mol) in 20 ml of dry acetone were added anhydrous K2CO3 (4.55 g, 0.033 mol) and benzylbromide (5.64 g, 0.033 mol). The resulting solution was refluxed for 5 h and the solvent evaporated under reduced pressure. The residue was partitioned between ether and water. The ether layer was washed with 10% aqueous NaOH solution and brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting residue was recrystallized from absolute ethanol affording 7.6 g (91.7%) of methyl 5-chloro-2-phenylmethoxybenzoate as white crystals: mp 54.5°-55° C.; IR (KBr) 1740 (ester) cm-1 ; NMR (CDCl3, 90 MHz) δ 3.90 (s, 3H, CO2CH3), 5.16 (s, 2H, OCH2Ph), 6.93 (d, 1H, ArH, J=8.9 Hz), 7.20-7.55 (m, 6H, ArH), 7.79 (d, 1H, ArH, J=2.9 Hz). Anal calcd. for (C15H13ClO3): C, 65.11; H, 4.73; Cl, 12.81. Found: C, 65.33; H, 4.88; Cl, 13.08.

Workup

  1. temperatureThe resulting solution was refluxed for 5 h
  2. customthe solvent evaporated under reduced pressure
  3. customThe residue was partitioned between ether and water
  4. washThe ether layer was washed with 10% aqueous NaOH solution and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was recrystallized from absolute ethanol affording 7.6 g (91.7%) of methyl 5-chloro-2-phenylmethoxybenzoate as white crystals

Sources & evidence

ORD record
ord-ea62bbba20b84f60bd78f66ba25d0443
Source dataset
uspto-grants-1989_07
Patent number
US04845121

Reaction notes

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