Triphenylphosphine → 4-pentoxyphenyl (2E)-3-{4-(6-chlorohexyloxy)phenyl}acrylate

HRID 2246017Notes

Reaction equation

HRID 2246017 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][CH:14]=2)=[O:11])=[CH:4][CH:3]=1.[Cl:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1.C1(C)C=CC=CC=1>[Cl:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:17][CH:18]=2)=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 748286-Chloro-1-hexanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 592174494-pentoxyphenyl (2E)-3-{4-hydroxyphenyl}acrylate

Product 1

HCID 592174574-pentoxyphenyl (2E)-3-{4-(6-chlorohexyloxy)phenyl}acrylateYield 74.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7.35 g (22.5 mmol) 4-pentoxyphenyl (2E)-3-{4-hydroxyphenyl}acrylate, 3.36 g (24.6 mmol) 6-chloro-1-hexanol and 6.45 g (24.6 mmol) of triphenylphosphine were dissolved in 100 ml of tetrahydrofurane. The colourless solution was subsequently cooled to 0° C. and 4.28 g (24.6 mmol) of a 40% solution of azodicarboxylic acid diethyl ester in toluene were added dropwise thereto over a period of 25 minutes. The mixture was subsequently allowed to react for 4 h at 0° C. The reaction mixture was reduced in volume by evaporation. The resulting residue was added to a mixture of methanol and water (3:2) and was then extracted with a mixture of tert.-butyl-methylether:hexane 1:1. The tert.-butyl-methylether:hexane phase was washed repeatedly with water, dried over magnesium sulphate, filtered and concentrated by rotary evaporation to yield 7.5 g 4-pentoxyphenyl (2E)-3-{4-(6-chlorohexyloxy)phenyl}acrylate as yellowish crystals.

Workup

  1. customto react for 4 h at 0° C
  2. customThe reaction mixture was reduced in volume by evaporation
  3. additionThe resulting residue was added to a mixture of methanol and water (3:2)
  4. extractionwas then extracted with a mixture of tert.-butyl-methylether:hexane 1:1
  5. washThe tert.-butyl-methylether:hexane phase was washed repeatedly with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-2a7432e3671346ceb845acac1c5cbf9f
Source dataset
uspto-grants-2010_03
Patent number
US07687118B2

Reaction notes

Loading…