Benzyl Bromide → HCID 12398565, compound

HRID 2252255Notes

Reaction equation

HRID 2252255 reaction equation
[C:1]1([O:7][C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:17]([O:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]([O:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:16])=[CH:14][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 87250Phenylparaben

Product 1

HCID 12398565HCID 12398565, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Hydroxy-benzoic acid phenyl ester (5 g, 23.3 mmol), benzyl bromide (5.54 mL, 46.7 mmol), K2CO3 (9.6 g, 70.0 mmol), and anhydrous acetone (200 mL) were mixed and reflux overnight. All acetone was removed. To the mixture was added water (300 mL). The solid was filtered, washed with methanol (50 mL×3), and dried to give the desired compound (6.63 g, 93%). MS (DCI) m/z 305 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 5.17 (s, 2H) 7.30-7.09 (m, 2H) 7.17-7.23 (m, 2H) 7.27 (m, 1H) 7.34-7.48 (m, 7H) 8.13-8.19 (m, 2H)

Workup

  1. temperaturereflux overnight
  2. customAll acetone was removed
  3. additionTo the mixture was added water (300 mL)
  4. filtrationThe solid was filtered
  5. washwashed with methanol (50 mL×3)
  6. customdried

Sources & evidence

ORD record
ord-64af7527d2934c698c11ad0c9b1d3af6
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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