Water → Methyl 4-(phenoxymethyl)benzoate

HRID 1781159

Reaction equation

HRID 1781159 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 925826Methyl 4-(phenoxymethyl)benzoateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of 5.72 g (25.0 mmol, 1.0 eq.) of methyl-4-bromomethylbenzoate and 3.80 g (27.5 mmol, 1.1 eq.) of K2CO3 in 10 mL of DMF at ambient temperature was added a solution of 2.59 g (27.5 mmol, 1.1 eq.) of phenol in 10 mL of DMF dropwise, and the mixture stirred overnight. The reaction mixture was poured into 100 mL of water and extracted with 3×100 mL portions of 25% CH2Cl2 -hexanes. The combined organic phases were washed with 3×100 mL portions of water, dried (MgSO4), filtered and concentrated. The solid residue was recrystallized from ~50 mL of hexanes to give 5.31 g (88%) of the title compound as a white, crystalline solid. 1H NMR (300 MHz, CDCl3) δ 8.05 (d, 2H), 7.51 (d, 2H), 7.26-7.33 (m, 2H), 6.95-7.02 (m, 3H), 5.13 (s, 2H), 3.92 (s, 3H). MS (DCl) m/e 260 (M+NH4)+.

Workup

  1. extractionextracted with 3×100 mL portions of 25% CH2Cl2 -hexanes
  2. washThe combined organic phases were washed with 3×100 mL portions of water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe solid residue was recrystallized from ~50 mL of hexanes

Sources & evidence

ORD record
ord-f184d13018f8412282d80e43650a7fd1
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Linked notes

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