Ammonia → 6-chlorohexyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate

HRID 523329Notes

Reaction equation

HRID 523329 reaction equation
N.C(OC([O:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][Cl:25])=[O:17])=[CH:10][CH:9]=1)=O)C>CC(C)=O.N1C=CC=CC=1>[OH:7][C:8]1[CH:9]=[CH:10][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][Cl:25])=[O:17])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 867326476-chlorohexyl(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoate

Product 1

HCID 867326486-chlorohexyl(2E)-3-(4-hydroxyphenyl)prop-2-enoateYield 100.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1049PyridineSolvent

Procedure

A 25% NH3 solution diluted in 780 mL of acetone is added dropwise to a solution of 89.3 g (247 mmol) of 6-chlorohexyl(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoate in 752 mL of pyridine. The mixture is allowed to stir for 20 hours at room temperature. The reaction mixture is then partitioned between ethylacetate and water. The organic phase is then washed repeatedly with water, dried over sodium sulfate, filtered off and concentrated by rotary evaporation. The solid is dried under vacuum to yield 70 g (100%) of pure 6-chlorohexyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate as a white powder.

Workup

  1. customThe reaction mixture is then partitioned between ethylacetate and water
  2. washThe organic phase is then washed repeatedly with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated by rotary evaporation
  6. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-1448c00ac21541c1a4a3da575b37b787
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Reaction notes

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