Triethylamine → Dibenzyl ether

HRID 2355804Notes

Reaction equation

HRID 2355804 reaction equation
C(OC1C=C2C(=CC=1)C=C(C(O)=O)C=C2)(=O)C=C.CS(Cl)(=O)=O.C(N(CC)CC)C.[CH2:31]([O:38][C:39]1[CH:44]=[CH:43][C:42](O)=[C:41]([CH2:46][CH2:47]C)C=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.CN(C)C1C=CN=CC=1>[CH2:39]([O:38][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:44]1[CH:43]=[CH:42][CH:41]=[CH:46][CH:47]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222611274-(Benzyloxy)-2-propylphenolHCID 592169606-[(1-Oxo-2-propen-1-yl)oxy]-2-naphthalenecarboxylic acid

Product 1

HCID 7657Dibenzyl ether

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Specifically, 1.90 g (7.86 mmol) of 6-acryloyloxy-2-naphthoic acid was dissolved in 10 g of THF, to which 0.99 g (8.65 mmol) of methanesulfonyl chloride was added with ice-water bath cooling, and further 1.91 g (18.87 mmol) of triethylamine (TEA) was added dropwise. After stirring for 1 hour, 10 mg (0.08 mmol) of 4-dimethylaminopyridine (DMAP) was added, to which a solution of 2.00 g (8.25 mmol) of 4-benzyloxy-2-n-propylphenol dissolved in 7 g of THF was added dropwise. After stirring for 1 hour, the reaction mixture was allowed to warm to room temperature, the precipitates were removed by filtration, and the filtrate was washed with water. After removing the solvent by evaporation, the residue was purified by column chromatography (developing solvent: dichloromethane, SiO2) and recrystallized from acetone. Thus the target benzyl ether was obtained as a white solid (2.27 g, 61.9% yield).

Workup

  1. additionwas added with ice-water bath
  2. temperaturecooling
  3. additionwas added dropwise
  4. stirringAfter stirring for 1 hour
  5. customthe precipitates were removed by filtration
  6. washthe filtrate was washed with water
  7. customAfter removing the solvent
  8. customby evaporation
  9. customthe residue was purified by column chromatography (developing solvent: dichloromethane, SiO2)
  10. customrecrystallized from acetone

Sources & evidence

ORD record
ord-9818a46524b1429882df66f61af5df2b
Source dataset
uspto-grants-2010_07
Patent number
US07754912B2

Reaction notes

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