Acetic Acid → HCID 14795882, compound

HRID 1288631Notes

Reaction equation

HRID 1288631 reaction equation
[CH2:1]([Sn:5]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[OH-].[K+].C(O)(=O)C.O>C(O)C>[CH2:20]([Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 13256035Methyl 4-(tributylstannyl)benzoate

Product 1

HCID 14795882HCID 14795882, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-tri-n-butylstannylbenzoate (3.0 g, 7 mmol) in absolute ethanol (60 ml) was added 0.25 g KOH (9 mmol). The resulting solution was refluxed for 2 hours. The solution was cooled and poured into an ice-cold solution of acetic acid (0.64 g, 10.6 mmol) and water (100 ml). The solution was then extracted with diethyl ether (80 ml). The ether phase was washed with water (30 ml), dried over MgSO4 (5 g), filtered and evaporated under reduced pressure to afford 2.6 g (88%) of the title compound. This material was used without further purification.

Workup

  1. temperatureThe resulting solution was refluxed for 2 hours
  2. temperatureThe solution was cooled
  3. extractionThe solution was then extracted with diethyl ether (80 ml)
  4. washThe ether phase was washed with water (30 ml)
  5. dry with materialdried over MgSO4 (5 g)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-871560983abd480daa5fe2479ef7f7f5
Source dataset
uspto-grants-1998_05
Patent number
US05746997

Reaction notes

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