Diethyl Ether → Methyl 3-butanoyl-4-hydroxybenzoate

HRID 14248Notes

Reaction equation

HRID 14248 reaction equation
[C:1]([CH:6]1[CH2:11][C:10](O)([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:7]1=[O:17])(=[O:5])[CH2:2][CH2:3][CH3:4].B(F)(F)F.O(CC)CC>C1C=CC=CC=1>[C:1]([C:6]1[CH:11]=[C:10]([CH:9]=[CH:8][C:7]=1[OH:17])[C:12]([O:14][CH3:15])=[O:13])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 21086214HCID 21086214, compound

Product 1

HCID 12533653Methyl 3-butanoyl-4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of methyl 5-butyryl-1-hydroxy-4-oxocyclohex-2-ene-1-carboxylate in benzene was added BF3.O(Et)2 (1.3 mL, 10 mmol). The mixture was stirred for 0.25 h and then quenched with saturated sodium bicarbonate followed by extraction with dichloromethane. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford methyl 3-butyryl-4-hydroxybenzoate which was used without further purification or characterization.

Workup

  1. customquenched with saturated sodium bicarbonate
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d45898382cf545c6a8d183ff834260e4
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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