4-Coumaric acid → HCID 57835753, compound

HRID 2235581Notes

Reaction equation

HRID 2235581 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, compound

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 A.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 A.2 (15 g). MS ESI (pos.) m/e: 405 (M+H). 1H NMR (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
  5. customto give A.2 (15 g)

Sources & evidence

ORD record
ord-9681d328540b4ba6b90c72f7ce9c3349
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

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