Water → Dimethyl 5-bentyloxy-isophthalate

HRID 393403Notes

Reaction equation

HRID 393403 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].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:16]([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:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 7643390Dimethyl 5-bentyloxy-isophthalateYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of dimethyl 5-hydroxyisophthalate (50.0 g, 238 mmol) in N,N-dimethylformamide (500 mL), benzyl bromide (29.5 mL, 248 mmol) was added dropwise in the presence of potassium carbonate (42.4 g, 307 mmol), and the reaction mixture was stirred for 2 hours at room temperature, followed by addition of water thereto. The resultant mixture was extracted with diethyl ether. The resultant organic layer was washed sequentially with water and saturated brine and dried over sodium sulfate anhydrate. The solvent was removed under reduced pressure, to thereby yield a solid. The solid was crystallized from diethyl ether, to thereby yield 68.9 g of dimethyl 5-benzyloxyisophthalate as colorless needles (yield 96%).

Workup

  1. extractionThe resultant mixture was extracted with diethyl ether
  2. washThe resultant organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over sodium sulfate anhydrate
  4. customThe solvent was removed under reduced pressure
  5. customto thereby yield a solid
  6. customThe solid was crystallized from diethyl ether

Sources & evidence

ORD record
ord-7b3e1301fdd14e548081913c51dbae47
Source dataset
uspto-grants-2004_10
Patent number
US06806395B2

Reaction notes

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