4-Coumaric acid → HCID 57835753, compound

HRID 1675241Notes

Reaction equation

HRID 1675241 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-9adda9d0cb15400a91f79f6a3fb851d8
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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