Hydrochloric Acid → 4-(3-Methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acid

HRID 29469Notes

Reaction equation

HRID 29469 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][CH2:18][O:19][CH3:20])[C:9]=2[C:10]=1[CH3:11])=[O:5])C.[Li+].[OH-].Cl>O1CCCC1.CO>[CH3:20][O:19][CH2:18][CH2:17][CH2:16][C:12]1[C:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[O:7][C:8]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 687130034-(3-Methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687109184-(3-Methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acidYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (2.213 g, 8.018 mol) in tetrahydrofuran (25 mL) and methanol (9 mL) at room temperature was added 1N LiOH (16.838 mL). The resulting yellow solution was stirred at room temperature for 2.5 hours, neutralized with 1N HCl and was then partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and reduced to dryness furnishing 1.98 g (98%) of 4-(3-methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acid as a white solid. MS (ES) m/z: 249.11214 (M+H)+, 497.21700 (2M+H).

Workup

  1. customwas then partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered

Sources & evidence

ORD record
ord-bbacfac85f904bb1b34739949c3af491
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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