4-Coumaric acid → 4-(6-Hydroxyhexyloxy)cinnamic acid

HRID 970247Notes

Reaction equation

HRID 970247 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[I-].[K+].[OH-].[K+].Cl[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]>C(O)C.O>[OH:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 3224-Coumaric acidHCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 748286-Chloro-1-hexanol

Product 1

HCID 673232894-(6-Hydroxyhexyloxy)cinnamic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
35 °C

Procedure

To a mixture of 24.62 g (0.15 mole) 4-hydroxycinnamic acid and 0.29 g (1.65 mmole) of potassium iodide in 60 ml of ethanol were added under a nitrogen atmosphere in 10 min a solution of 20.72 g (0.314 mole) of potassium hydroxide in 60 ml of water using a dropping funnel. The resulting solution was heated to 30-40° C. and 6-chlorohexanol (22.54 g, 0.165 mole) was then added in about 10 min. The solution was then refluxed overnight. After cooling, 70 ml of water were added to the solid reaction mixture, and the ethanol was removed using a rotary evaporator. The residue was cooled in an ice/water bath and 70 ml of conc. hydrochloric acid were added under stirring. The solid was collected and washed with water. Then the solid was stirred at 50° C. with 250 ml of acetone. After drying at 100° C. in vacuo 24.5 g (62%) of product 13 were obtained.

Workup

  1. temperatureThe solution was then refluxed overnight
  2. temperatureAfter cooling
  3. customthe ethanol was removed
  4. customa rotary evaporator
  5. temperatureThe residue was cooled in an ice/water bath
  6. addition70 ml of conc. hydrochloric acid were added
  7. customThe solid was collected
  8. washwashed with water
  9. stirringThen the solid was stirred at 50° C. with 250 ml of acetone
  10. dry with materialAfter drying at 100° C. in vacuo 24.5 g (62%) of product 13
  11. customwere obtained

Sources & evidence

ORD record
ord-16c714b17f2e4467837bf02c65194e0b
Source dataset
uspto-grants-2007_12
Patent number
US07311948B2

Reaction notes

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