Benzyl Bromide → Dimethyl 5-bentyloxy-isophthalate

HRID 852543Notes

Reaction equation

HRID 852543 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][O:16][C:17](=[O:29])[C:18]1[CH:27]=[C:26]([OH:28])[CH:25]=[C:20]([C:21]([O:23][CH3:24])=[O:22])[CH:19]=1>CC(C)=O>[CH3:24][O:23][C:21](=[O:22])[C:20]1[CH:25]=[C:26]([O:28][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:27]=[C:18]([C:17]([O:16][CH3:15])=[O:29])[CH:19]=1

Participants

5

Reactant 3

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

Product 1

HCID 7643390Dimethyl 5-bentyloxy-isophthalateYield 105.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (21 g, 153 mmol, 2 equiv) and benzyl bromide (11 ml, 92 mmol, 1.2 equiv) were added to a solution of 5-hydroxy-isophthalic acid dimethyl ester (D42) (16.1 g, 76.7 mmol, 1 equiv) in acetone (400 ml) at room temperature. The resulting solution was refluxed for 18 h, cooled to room temperature and concentrated in vacuo. The residue was partitioned between H2O and AcOEt. The aqueous phase was extracted with AcOEt and the combined organic layers were washed with 2N aqueous NaOH solution and brine, dried over MgSO4 and concentrated in vacuo to give 5-benzyloxy-isophthalic acid dimethyl ester (D44) (24.2 g, 105%) as a white solid. [M+H]+=301.0, RT=3.50 min

Workup

  1. temperatureThe resulting solution was refluxed for 18 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between H2O and AcOEt
  4. extractionThe aqueous phase was extracted with AcOEt
  5. washthe combined organic layers were washed with 2N aqueous NaOH solution and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71d980f29f114cd18960011bb8d0f879
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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