Methanol → Methyl 4-(benzyloxy)butanoate

HRID 968820Notes

Reaction equation

HRID 968820 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:20]O>>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:20])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5622014-(Benzyloxy)butanoic acid

Product 1

HCID 562189Methyl 4-(benzyloxy)butanoate

Procedure

To a solution of 4-benzyloxybutyric acid (54.8 g, 0.282 mol) in methanol (1.4 L), was added sulfuric acid (concentrated, 1.4 mL) dropwise and it was stirred at room temperature under nitrogen overnight. The reaction mixture was concentrated on a rota-vapor, the residue was then partitioned between ethyl acetate (700 mL) and saturated sodium bicarbonate aqueous solution (200 mL). The organic phase was separated, washed with brine (2×100 mL), then dried over Na2SO4 and filtered. Evaporation of solvent gave the titled compound as an oil that was used in step B without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated on a rota-vapor
  2. customthe residue was then partitioned between ethyl acetate (700 mL) and saturated sodium bicarbonate aqueous solution (200 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-aba2052c3ddd45d4aa9fb507ad5f07e7
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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