Benzyl Bromide → Dimethyl 5-bentyloxy-isophthalate

HRID 852543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852543
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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 7643390Dimethyl 5-bentyloxy-isophthalateAusbeute 105,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-71d980f29f114cd18960011bb8d0f879
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253198B2

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