Benzyl Bromide → Methyl 3-[4-(benzyloxy)phenyl]propanoate

HRID 2227891Notes

Reaction equation

HRID 2227891 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Product 1

HCID 525519Methyl 3-[4-(benzyloxy)phenyl]propanoateYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride in DMF (50 ml) at 0° C. was added dropwise a solution of methyl 3-(4-hydroxyphenyl)propionate (10.0 g, 55.5 mmol) and benzyl bromide (7.93 ml, 66.7 mmol) dissolved in DMF (100 ml). The mixture was stirred at room temperature for 16 hours, cooled to 0° C., quenched with aqueous ammonium chloride (50 ml) and extracted with ethyl acetate (2×150 ml). The combined organic layers were washed with aqueous ammonium chloride (50 ml), brine (3×60 ml), dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from hexane-ethyl acetate to give the title compound (13.7 g, 91%) as a white solid.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with aqueous ammonium chloride (50 ml)
  3. extractionextracted with ethyl acetate (2×150 ml)
  4. washThe combined organic layers were washed with aqueous ammonium chloride (50 ml), brine (3×60 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-3fa6af6525d84cae854d3d31908ab35b
Source dataset
uspto-grants-2002_07
Patent number
US06414179B1

Reaction notes

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