Benzyl Bromide → HCID 18434030, compound

HRID 1953194Notes

Reaction equation

HRID 1953194 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[O:11][C:10](=[O:20])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CO>[CH2:24]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[O:11][C:10](=[O:20])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10942334Sodium MethoxideHCID 18434036HCID 18434036, compound

Product 1

HCID 18434030HCID 18434030, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

4-[3'-(hydroxy)phenyl]-7-methoxycoumarin (prepared as in Example 1 (ii) (268 g) and 95% sodium methoxide (102 g) were dissolved in methanol (3.00 L) and stirred while heating to 45° C. Benzyl bromide (314 g) was added and the reaction was heated to 60° C. A thick precipitate formed in the pink reaction mixture. After 3 hours, the slurry was cooled in an ice-water bath and filtered to collect the product, which was washed with methanol (500 mL) and water (1.0 L), then dried under vacuum (20 inches of Hg) at 70° C. to give 4-[3-(benzyloxy)phenyl]-7-methoxycoumarin (320 g, 89%).

Workup

  1. temperaturethe reaction was heated to 60° C
  2. customA thick precipitate formed in the pink reaction mixture
  3. temperaturethe slurry was cooled in an ice-water bath
  4. filtrationfiltered
  5. customto collect the product, which
  6. washwas washed with methanol (500 mL) and water (1.0 L)
  7. customdried under vacuum (20 inches of Hg) at 70° C.

Sources & evidence

ORD record
ord-2b62ac8ba5174a86a65f4c74c65ec36a
Source dataset
uspto-grants-2000_09
Patent number
US06114549

Reaction notes

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