Potassium Carbonate → HCID 18331486, compound

HRID 858312Notes

Reaction equation

HRID 858312 reaction equation
OC1C=C(OC)C=CC=1[C:10]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:11]=1[C:17]([C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][C:20]=1C1C=CC(OC)=CC=1O)=O.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][C:43]([OH:45])=[O:44])=[CH:38][CH:37]=1.[C:46]([O-:49])([O-])=O.[K+].[K+].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C1C=CN=CC=1.CN(C=O)C.O>[Cl:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[C:43](=[O:45])[O:44][C:24]3[C:19]([C:17]=2[C:11]2[CH:12]=[CH:13][C:14]([OH:16])=[CH:15][CH:10]=2)=[CH:20][CH:21]=[C:22]([O:49][CH3:46])[CH:23]=3)=[CH:40][CH:41]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 15880(4-Chlorophenyl)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 69330296HCID 69330296, compound

Product 1

HCID 18331486HCID 18331486, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2-hydroxy-4-methoxyphenyl-4-hydroxyphenyl ketone (2.6 grams, 10.65 mmol), 4-chlorophenylacetic acid (4.0 g, 23.43 mmol), K2CO3 (4.4 g, 31.95 mnol), carbonyldiimidazole (3.8 g, 23.43 m.mol), and 4-dimethylaminopyridine (0.1 g) in 20 mL of DMF was warmed at 90° C. for 5 hours. The reaction mixture was poured into 150 mL of H2O and stirred for 30 minutes. The precipitated product was collected by filtration and the purified desired product was isolated following flash chromatography (2.1 g, 52%, LC/MS=379 (M+H+)).

Workup

  1. filtrationThe precipitated product was collected by filtration
  2. customthe purified desired product
  3. customwas isolated

Sources & evidence

ORD record
ord-9c902bb0f2794083a8e7601e90782fb3
Source dataset
uspto-grants-2006_12
Patent number
US07148252B2

Reaction notes

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