Ethylparaben → Ethyl 4-(1,3-diphenyl-1-propoxy)benzoate

HRID 363015

Reaction equation

HRID 363015 reaction equation
[C:1]1([CH:7]([OH:16])[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]1([CH:7]([O:16][C:18]2[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=2)[CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2501291,3-Diphenylpropan-1-ol

Product 1

HCID 54012855Ethyl 4-(1,3-diphenyl-1-propoxy)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-2 (2.12 g, 10.0 mmol) in tetrahydrofuran (25 ml) under a nitrogen atmosphere was added ethyl 4-hydroxybenzoate (6-3) (1.66 g, 10.0 mmol) followed by triphenyl phosphine (3.15 g, 12.0 mmol). The mixture was cooled in an ice bath and diethyl azodicarboxylate (2.09 g, 12 mmol) was added. This mixture was stirred overnight at ambient temperature and the solvent was removed in vacuo. The residue was taken up in the water and the ether layer was separated, washed with sodium bicarbonate and water, dried, filtered and concentrated in vacuo to yield an oil. Chromatographic purification on silica gel gave 6-4 as a colorless oil.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customthe solvent was removed in vacuo
  3. customthe ether layer was separated
  4. washwashed with sodium bicarbonate and water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield an oil
  9. customChromatographic purification on silica gel

Sources & evidence

ORD record
ord-8e8a492bb8234a83a808a9f25992f984
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Linked notes

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