Lithium hydroxide, monohydrate → 5-[[4-(4-methylphenyl)phenoxy]methyl]furan-2-carboxylic Acid

HRID 899518Notes

Reaction equation

HRID 899518 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)=[O:5])C.O.[OH-].[Li+]>O1CCCC1.CO.O>[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:8]3[O:7][C:6]([C:4]([OH:5])=[O:3])=[CH:10][CH:9]=3)=[CH:14][CH:15]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 596949875-(4'-Methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid ethyl ester

Product 1

HCID 71388535-[[4-(4-methylphenyl)phenoxy]methyl]furan-2-carboxylic AcidYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-(4′-methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid ethyl ester (2.00 g, 5.9 mmol) in tetrahydrofuran (30 mL) and methanol (10 mL) was added to a solution of lithium hydroxide monohydrate (0.476 g, 11.3 mmol) in water (15 mL). Methanol (5 mL) and tetrahydrofuran (10 mL) were added, and the reaction mixture was stirred at room temperature overnight. The solvents were evaporated, and the residue was suspended in water and acidifed to pH 2.5 with 1 M HCl. The resulting white solid was filtered off, and twice suspended in ethyl acetate and evaporated to give 5-(4′-methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid (1.6 g, 88%) as a white solid.

Workup

  1. customThe solvents were evaporated
  2. filtrationThe resulting white solid was filtered off
  3. customevaporated

Sources & evidence

ORD record
ord-6de07e99f9024d52be400a55251b5072
Source dataset
uspto-grants-2008_04
Patent number
US07355049B2

Reaction notes

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