Methylparaben → Methyl 4-(4-phenylbutoxy)benzoate

HRID 1603918Notes

Reaction equation

HRID 1603918 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]1([CH2:18][CH2:19][CH2:20][CH2:21]O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)C>[C:12]1([CH2:18][CH2:19][CH2:20][CH2:21][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 76889BenzenebutanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 10978973Methyl 4-(4-phenylbutoxy)benzoateYield 70%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-hydroxybenzoate (3 g, 19.7 mmol), 4-phenylbutanol (3.04 ml, 19.7 mmol) and triphenylphosphine (7.74 g, 29.6 mmol) in anhydrous tetrahydrofuran (110 ml) was added with diethyl azodicarboxylate (4.65 ml, 29.6 mmol). The resulting mixture was left under stirring at room temperature for 36 h, then was added with ethyl ether (500 ml) and left to crystallize for 24 hours at 0° C. After that the solid was filtered and the filtrate was washed successively with 0.2M hydrochloric acid, 5% sodium bicarbonate and a sodium chloride saturated solution. After drying and removing the solvent under reduced pressure, a residue was obtained which was purified by chromatography through a silica gel column, eluting with petroleum ether:chloroform mixtures of increasing polarity, thereby recovering 3.856 g of the title compound (70% yield).

Workup

  1. waitThe resulting mixture was left
  2. waitleft
  3. customto crystallize for 24 hours at 0° C
  4. filtrationAfter that the solid was filtered
  5. washthe filtrate was washed successively with 0.2M hydrochloric acid, 5% sodium bicarbonate
  6. customAfter drying
  7. customremoving the solvent under reduced pressure
  8. customa residue was obtained which
  9. customwas purified by chromatography through a silica gel column
  10. washeluting with petroleum ether
  11. temperaturechloroform mixtures of increasing polarity

Sources & evidence

ORD record
ord-31d4dcb50b7441dca6a7e11a22af0522
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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