Benzyl Bromide → HCID 20059716, compound

HRID 1085551Notes

Reaction equation

HRID 1085551 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]([OH:12])=[O:11])=[C:4]([CH3:13])[CH:3]=1.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:9][C:10]([O:12][CH2:13][C:4]2[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=2)=[O:11])=[C:6]([CH3:8])[CH:7]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 126604274-Hydroxy-2,6-dimethylbenzeneacetic acid

Product 1

HCID 20059716HCID 20059716, compoundYield 161.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.36 g of 2-(4-hydroxy-2,6-dimethylphenyl)acetic acid was treated with 184 mg of a 60% dispersion of sodium hydride in mineral oil and 0.72 g of benzyl bromide in 10 ml of dry dimethylformamide. The solvent was removed by evaporation and the residue was partitioned between water and methylene chloride. The organic layer was evaporated to give 0.63 g of crude product of melting point 54°-57° C. Recrystallization from aqueous methanol gave 0.58 g of pure benzyl 2-(4-benzyloxy-2.6-dimethylphenyl)acetate of melting point 62°-64° C.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between water and methylene chloride
  3. customThe organic layer was evaporated
  4. customto give 0.63 g of crude product of melting point 54°-57° C
  5. customRecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-b2af7a42e55841c9a65aff3f57137c49
Source dataset
uspto-grants-1991_04
Patent number
US05010060

Reaction notes

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