Benzyl Bromide → HCID 69913482, compound

HRID 431368Notes

Reaction equation

HRID 431368 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12](O)[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.C(Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24](=O)([O-])[O-:25].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([CH2:24][O:25][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 69913482HCID 69913482, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-hydroxyisophthalic acid dimethyl ester (700 mg; 3.33 mmol), benzyl bromide (635 mg; 3.70 mmol), and potassium carbonate (510 mg; 3.7 mmol) in acetone was refluxed overnight. After cooling, the mixture was partitioned between water and ethyl acetate. The layers were separated, the aqueous layer was extracted twice more with ethyl acetate, and the combined organic portions were washed with brine, dried, and concentrated to provide a crude solid. Recrystallization from ethyl acetate/hexanes furnished the product as a white crystalline material, mp 95-97° C., 1H NMR (400 MHz): d 3.94 (s, 6H); 5.15 (s, 2H): 7.42 (m, 5H); 7.84 (s, 2H); 8.29 (s, 1H).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between water and ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted twice more with ethyl acetate
  6. washthe combined organic portions were washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customto provide a crude solid
  10. customRecrystallization from ethyl acetate/hexanes
  11. customfurnished the product as a white crystalline material, mp 95-97° C., 1H NMR (400 MHz): d 3.94 (s, 6H); 5.15 (s, 2H)

Sources & evidence

ORD record
ord-07d5b31889fb4de681a604397035225a
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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