Methylparaben → HCID 69638743, compound

A solution of 14.36 g (82.5 mmol) of diethyl-azo-dicarboxylate in 50 ml of tetrahydrofuran was added within 30 minutes to a solution of 11.4 g (75.0 mmol) 4-hydroxy-benzoic acid methyl ester, 20.65 g (78.8 mmol) of triphenylphosphin and 13.5 g (75.0 mmol) of 4-benzyloxy-1-butanol dissolved in 100 ml of tetrahydrofuran. The reaction mixture was then stirred for 1 hour at room temperature, 1 g of triphenylphosphin was added and stirring continued for 1 hour at room temperature and for 30 minutes at reflux. The reaction mixture was then diluted with 200 ml of hexane and filtered. The filtrate was poured into 200 ml of a saturated potassium carbonate solution and extracted 3 times with 200 ml of ethylacetate. The combined ethylacetate phases were washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 98:2 v/v mixture of dichloromethane and ether as the eluent giving 21.8 g (92.4%) 4-(4-benzyloxy-butoxy)-benzoic acid methyl ester as colorless viscous oil, MS: 314 (M+).

1. stirringstirring
2. waitcontinued for 1 hour at room temperature and for 30 minutes
3. temperatureat reflux
4. filtrationfiltered
5. additionThe filtrate was poured into 200 ml of a saturated potassium carbonate solution
6. extractionextracted 3 times with 200 ml of ethylacetate
7. washThe combined ethylacetate phases were washed with brine
8. dry with materialdried over magnesium sulfate
9. customevaporated under reduced pressure
10. customThe residue formed
11. customwas chromatographed on silica gel with a 98:2 v/v mixture of dichloromethane and ether as the eluent

ORD record

ord-4af37616f7a14931adc2dcd326ab97cd

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06953806B2