Hydrochloric Acid → 4-pentoxyphenyl (2E)-3-{4-hydroxyphenyl}acrylate

HRID 2246016Notes

Reaction equation

HRID 2246016 reaction equation
C(OC([O:6][C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:20][CH:19]=2)=[O:16])=[CH:9][CH:8]=1)=O)C.N1C=CC=CC=1.[OH-].[NH4+].Cl>O.CC(C)=O>[OH:6][C:7]1[CH:8]=[CH:9][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:22][CH:23]=2)=[O:16])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14923Ammonium HydroxideHCID 592174614-pentoxyphenyl (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}acrylate

Product 1

HCID 592174494-pentoxyphenyl (2E)-3-{4-hydroxyphenyl}acrylateYield 96%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

7.65 g (23.45 mmol) 4-pentoxyphenyl (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}acrylate, 70 ml pyridine and 40 ml acetone were mixed. A solution of 12.5 ml ammonium hydroxide 25% in water and 30 ml acetone were added dropwise. The reaction mixture was subsequently allowed to react for 18 h at 25° C. and acidified to pH=1 with hydrochloric acid 7 N. The product was filtered off, washed with water and dried under vacuum to give 7.35 g 4-pentoxyphenyl (2E)-3-{4-hydroxyphenyl}acrylate as colourless powder.

Workup

  1. customto react for 18 h at 25° C.
  2. filtrationThe product was filtered off
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-9105e53ac79644189920f29aac29fc5b
Source dataset
uspto-grants-2010_03
Patent number
US07687118B2

Reaction notes

Loading…