Lithium Hydroxide → 3-(Benzyloxy)-5-{[(2S)-1-methoxybutan-2-yl]oxy}benzoic acid

HRID 1990207Notes

Reaction equation

HRID 1990207 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([O:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=1)[C:11]([O:13]C)=[O:12])[CH2:5][CH3:6].C1COCC1.[OH-].[Li+]>O.CO>[CH3:1][O:2][CH2:3][C@@H:4]([O:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:17]=1)[C:11]([OH:13])=[O:12])[CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 53629657methyl 3-({(1S)-1-[(methyloxy)methyl]propyl}oxy)-5-[(phenylmethyl)oxy]benzoate

Product 1

HCID 591270993-(Benzyloxy)-5-{[(2S)-1-methoxybutan-2-yl]oxy}benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 3-({(1S)-1-[(methyloxy)methyl]propyl}oxy)-5-[(phenylmethyl)oxy]benzoate (6.85 g, 20 mmol) in 3:1 THF:methanol (100 mL) was added 1N lithium hydroxide solution in water (40 mL, 40 mmol), then a further 100 mL water was added portionwise at intervals while the resulting mixture was stirred for 2 hours. The organic solvents were removed by evaporation and the cloudy solution filtered. The pH of the filtrate was adjusted to 3 by the addition of 2 M hydrochloric acid. This was extracted with ethyl acetate (3×70 mL). The combined organic extracts were dried (MgSO4) and evaporated to afford the title compound as a colourless oil which solidified (6.36 g,).

Workup

  1. customThe organic solvents were removed by evaporation
  2. filtrationthe cloudy solution filtered
  3. additionThe pH of the filtrate was adjusted to 3 by the addition of 2 M hydrochloric acid
  4. extractionThis was extracted with ethyl acetate (3×70 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-a0aed44f8a6d4d7cba1aba5b4879e130
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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