Hydrochloric Acid → HCID 20745900, compound

HRID 2308128Notes

Reaction equation

HRID 2308128 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH2:17][OH:18])[CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=1.[CH3:19][O:20][C:21](=[O:33])/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27](O)=[C:26]([O:31][CH3:32])[CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[CH3:19][O:20][C:21](=[O:33])/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([O:16][CH2:15][C:13]2[CH:12]=[C:11]([CH2:17][OH:18])[CH:10]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[CH:14]=2)=[C:26]([O:31][CH3:32])[CH:25]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5357283Methyl FerulateHCID 22603515HCID 22603515, compound

Product 1

HCID 20745900HCID 20745900, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.7 g (10 mmol) [3-[(6-chlorohexyl)oxy]-5-[hydroxymethyl]phenyl] methanol (Example 6) were added to a solution of 2.6 g (12.5 mmol) (E)-4-hydroxy-3-methoxycinnamic acid methyl ester (Example 1) and 3.38 g (12.5 mmol) triphenylphosphine in 40 ml tetrahydrofuran. The colourless solution was cooled to 0° C. and then 5.2 ml (12.5 mmol) of a 40% solution of azodicarboxylic acid diethyl ester in toluene were added dropwise over a period of 2 hours. The mixture was allowed to react for 2 hours at 0° C. and then for 15 hours at room temperature. The reaction mixture was poured into an ice cold 1 M solution of HCl. The aqueous phase was extracted three times with a mixture of tert-butyl-methylether/ethyl acetate. The organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water, dried over magnesium sulfate, filtered and concentrated in vacuum. Purification of the residue by column chromatography on silica gel using hexane:ethyl acetate (1:1) as eluent yielded 2.2 g (48%) of (E)-3-[4-[3-[(6-chlorohexyl)oxy]-5-[hydroxymethyl]benzyloxy]-3-methoxyphenyl]acrylic acid methyl ester as an oily product that solidified on standing.

Workup

  1. customto react for 2 hours at 0° C.
  2. extractionThe aqueous phase was extracted three times
  3. additionwith a mixture of tert-butyl-methylether/ethyl acetate
  4. washThe organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-ce355bdf19e34d33a841fb2a01046465
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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