Hydrochloric Acid → 4-(6-Hydroxyhexyloxy)cinnamic acid

HRID 1441200Notes

Reaction equation

HRID 1441200 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22].Cl>O.CO>[OH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3224-Coumaric acidHCID 14798Sodium HydroxideHCID 779706-Bromo-1-hexanol

Product 1

HCID 673232894-(6-Hydroxyhexyloxy)cinnamic acidYield 78.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 4.4 g of NaOH in 20 ml of distilled water was added to a solution of 7.5 g of 4-hydroxy cinnamic acid in methanol, 0.02 g of Kl was added thereto, and then 10.0 g of 6-bromo-1-hexanol was slowly added dropwise for reaction at 65° C. for 24 hours. 100 ml of distilled water was added thereto to complete the reaction, and then the mixture was cooled to normal temperature. A 10% aqueous HCl solution was added thereto, and the obtained precipitants were filtered to obtain 9.5 g of 4-((6-hydroxyhexyl)oxy)cinnamic acid. (Yield: 60%)

Workup

  1. additionwas added
  2. customthe reaction
  3. temperaturethe mixture was cooled to normal temperature
  4. filtrationthe obtained precipitants were filtered

Sources & evidence

ORD record
ord-811cbea218cc4a32af435655dc420360
Source dataset
uspto-grants-2010_02
Patent number
US07655284B2

Reaction notes

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