Benzyl Bromide → Dimethyl 5-bentyloxy-isophthalate

HRID 2071032Notes

Reaction equation

HRID 2071032 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C([O-])([O-])=O.[K+].[K+].[CH:22]1[CH:27]=[CH:26][C:25]([CH2:28]Br)=[CH:24][CH:23]=1>CN(C=O)C>[CH2:28]([O:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:12]([O:14][CH3:15])=[O:13])[C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=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 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.98 g (9.42 mmol) of dimethyl 5-hydroxyisophthalate 3.0 g (21.7 mmol) of K2CO3 and 1.8 mL (15.1 mmol) of BnBr in 30 mL of DMF was heated at 60° C. for 18 h. After the mixture was filtered through cotton, water and CHCl3 were added. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (15% EtOAc/hexanes) provided the 2.64 g of dimethyl 5-(benzyloxy)isophthalate as a colorless solid in 93% yield.

Workup

  1. filtrationAfter the mixture was filtered through cotton, water and CHCl3
  2. additionwere added
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a644c0de062248dbb7f3f2638b159b8a
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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