Lithium hydroxide, monohydrate → 5-[(4-Phenylphenoxy)methyl]furan-2-carboxylic acid
Reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[O:9][C:10]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)=[CH:11][CH:12]=1)=[O:7]>O.O1CCCC1>[C:18]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:10]2[O:9][C:8]([C:6]([OH:7])=[O:5])=[CH:12][CH:11]=2)=[CH:20][CH:19]=1Participants
Procedure
A solution of lithium hydroxide monohydrate (5.10 g, 121.5 mmol) in water (50 mL) was added to a solution of 5-(biphenyl-4-yloxymethyl)-furan-2-carboxylic acid methyl ester (15.00 g, 48.6 mmol) in tetrahydrofuran (450 mL). The reaction mixture was stirred at room temperature for 72 h. The solvents were evaporated and water was added. The mixture was extracted three times with ether. Insoluble white solid was filtered off. The pH of the aqueous solution was adjusted to 3 and the resulting mixture was extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with 50% saturated brine and then evaporated under reduced pressure to give 5-(biphenyl-4-yloxymethyl)-furan-2-carboxylic acid (12.0 g, 84%) as a white solid.
Workup
- customThe solvents were evaporated
- additionwater was added
- extractionThe mixture was extracted three times with ether
- filtrationInsoluble white solid was filtered off
- extractionthe resulting mixture was extracted with ethyl acetate (3×500 mL)
- washThe combined organic layers were washed with 50% saturated brine
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-1965be05fd334f7087ab545fb4bf1a15
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07355049B2
Reaction notes
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