Water → Dimethyl 5-(allyloxy)isophthalate

HRID 1643828Notes

Reaction equation

HRID 1643828 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.[Cs+].[Cs+].[CH2:22](Br)[CH:23]=[CH2:24].O>CN(C=O)C>[CH2:24]([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])[CH:23]=[CH2:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 10933919Dimethyl 5-(allyloxy)isophthalateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of dimethyl 5-hydroxy-isophthalate (10 g, 47.577 mmol), Cs2CO3 (31 g, 95.2mmol) in DMF was added allyl bromide (4.83 mL, 57.1 mmol) drop-wise. After stirring the mixture for 14 hours, the reaction was treated with water, extracted with EtOAc (2×). The combined organic extract was dried over sodium sulfate, filtered and evaporated to provide the desired product as white solid (12 g, 100% yield). The crude product was used without further purification. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.94 (s, 6 H) 4.56-4.71 (m, 2 H) 5.33 (dd, J=10.46, 1.41 Hz, 1 H) 5.39-5.53 (m, 1 H) 5.96-6.17 (m, 1 H) 7.76 (d, J=1.32 Hz, 2 H) 8.28 (t, J=1.41 Hz, 1 H); LC-MS: (ESI)+m/z=251.00 (M+1)+.

Workup

  1. extractionextracted with EtOAc (2×)
  2. extractionThe combined organic extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-422268dbb6884f42a7d1013244ddaba1
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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