Benzyl Bromide → HCID 22116409, compound

HRID 481577Notes

Reaction equation

HRID 481577 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O.O>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH2:11][C:4]2[CH:5]=[CH:9][CH:10]=[CH:2][CH:3]=2)=[O:12])[C:5](=[CH:9][CH:10]=1)[C:6]([O:8][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:7])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 118814-Hydroxyphthalic acid

Product 1

HCID 22116409HCID 22116409, compoundYield 165.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4-Hydroxyphthalic acid (3.50 g, 19.2 mmol) and K2CO3 (23.9 g, 173 mmol) in acetone (100 mL) and water (50 mL) were stirred at rt for 15 min. Benzyl bromide (20.6 mL, 173 mmol) was added and the mixture was heated under reflux for 3 d. Vacuum distillation (45°-50° C./1.1 mm) removed residual benzyl alcohol and the distillation residue was purified by gradient flash chromatography (10-30% ethyl acetate:hexane) to give dibenzyl 4-benzyloxyphthalate (7.20 g, 83%) as a pale yellow oil. TLC Rf 0.65 (25% ethyl acetate:hexane). ##STR413## Step 2

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 d
  3. distillationVacuum distillation (45°-50° C./1.1 mm)
  4. customremoved residual benzyl alcohol
  5. distillationthe distillation residue was purified by gradient flash chromatography (10-30% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-1a2ff5d7c43244fb927c4d8f7b52a93b
Source dataset
uspto-grants-1998_08
Patent number
US05789434

Reaction notes

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