Triphenylphosphine → HCID 69037208, compound

HRID 1797337Notes

Reaction equation

HRID 1797337 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[O:14][CH3:15].[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]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:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[O:14][CH3:15]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 900121-Octanol, 8-chloro-HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5357283Methyl Ferulate

Product 1

HCID 69037208HCID 69037208, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

20.0 g (96.06 mmol) methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate, 16.6 g (100.9 mmol) 8-chlor-1-octanol and 27.7 g (105.7 mmol) of triphenylphosphine were dissolved in 400 ml of tetrahydrofurane. The colorless solution was subsequently cooled to 0° C. and 46.0 g (105.7 mmol) of a 40% solution of azodicarboxylic acid diethyl ester in toluene was added dropwise thereto over a period of 25 minutes. The mixture was subsequently allowed to react for 4 hours at 0° C. The reaction mixture 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 sulfate, filtered and concentrated by rotary evaporation. The crude product was recrystallised from 2-propanol yielded 30.8 g (90%) methyl (2E)-3-{4-[(8-chloroctyl)oxy]-3-methoxyphenyl}-2-propenoate as white crystals.

Workup

  1. customto react for 4 hours at 0° C
  2. customThe reaction mixture 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 sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe crude product was recrystallised from 2-propanol

Sources & evidence

ORD record
ord-7fc34bfe13f94b629ec6e45cce6ee5ee
Source dataset
uspto-grants-2006_04
Patent number
US07034098B2

Reaction notes

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