4-Coumaric acid → HCID 57835753, compound

HRID 2246661Notes

Reaction equation

HRID 2246661 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:18]=[CH:17][C:11]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=1.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1.O>CN(C=O)C>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][O:7][C:8]2[CH:9]=[CH:10][C:11](/[CH:12]=[CH:13]/[C:14]([O:16][CH2:12][C:11]3[CH:17]=[CH:18][C:8]([O:4][CH3:1])=[CH:9][CH:10]=3)=[O:15])=[CH:17][CH:18]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 3224-Coumaric acidHCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 57835753HCID 57835753, compoundYield 194.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (21 g, 152 mmol) was added to a mixture of 4-hydroxycinnamic acid 6.1 (6.25 g, 38.1 mmol) and p-methoxy benzyl chloride (10.35 mL, 76 mmol) in DMF (100 mL). The mixture was stirred at 80° C. for five hours. After cooling, the mixture was poured into water (700 mL). The solid was collected by filtration, washed with water and dried to give 6.2 (15 g). MS ESI (pos.) m/e: 405 (M+H). 1HNMR (CDCl3) δ 7.68 (d, 1H), 7.47 (d, 2H), 7.38 (m, 4H), 6.95 (m, 6H), 6.35 (d, 1H), 5.20 (s, 2H), 5.03 (s, 2H), 3.84 (s, 3H), 3.83 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-9a638a02bdd54ad3bd4a6add437797a4
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

Loading…