Methylparaben → methyl 4-[1-(S)-(4-isobutylphenyl)butoxy]benzoate

HRID 1956755Notes

Reaction equation

HRID 1956755 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([OH:15])[CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].O[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.O1CCCC1.O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]([O:15][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)[CH2:12][CH2:13][CH3:14])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11063606HCID 11063606, compound

Product 1

HCID 18663759methyl 4-[1-(S)-(4-isobutylphenyl)butoxy]benzoateYield 79.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(R)-(4-isobutylphenyl)butanol (1.13 g), methyl 4-hydroxybenzoate (917 mg) and triphenylphosphine (1.58 g) in toluene (40 ml) and tetrahydrofuran (10 ml) was added diethyl azodicarboxylate (0.95 ml) at -20° C. The mixture was stirred at -15°--20° C. for 1.5 hours and then added water (0.5 ml). The mixture was evaporated, dissolved in a mixture of n-hexane and ethyl acetate (4:1), filtered off and evaporated. The residue was chromatographed on silica gel eluting with a mixture of n-hexane and dichloromethane (1:1) to give methyl 4-[1-(S)-(4-isobutylphenyl)butoxy]benzoate as an oil (1.48 g).

Workup

  1. customThe mixture was evaporated
  2. dissolutiondissolved in a mixture of n-hexane and ethyl acetate (4:1)
  3. filtrationfiltered off
  4. customevaporated
  5. customThe residue was chromatographed on silica gel eluting with a mixture of n-hexane and dichloromethane (1:1)

Sources & evidence

ORD record
ord-c13e524eb7ca4fd483ed7534bb80ee3c
Source dataset
uspto-grants-1998_07
Patent number
US05780633

Reaction notes

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