Ethyl Acetate → 1-Phenylcyclobutanecarboxylic acid

HRID 1375092Notes

Reaction equation

HRID 1375092 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:16]([OH:18])=[O:17])[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.C(OCC)(=O)C>[Pd].C(O)(C)C.O>[C:9]1([C:12]2([C:16]([OH:18])=[O:17])[CH2:13][CH2:14][CH2:15]2)[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 6027611-(p-Chlorophenyl)cyclobutanecarboxylic acidHCID 2723923Ammonium formate2×

Product 1

HCID 2771711-Phenylcyclobutanecarboxylic acidYield 73.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent3×HCID 3776IsopropanolSolvent2×

Conditions

Temperature
65 °C

Procedure

A stirred suspension of palladium on carbon (3.6 g, 5%) in isopropanol (200 mL) was treated in one portion with a solution of ammonium formate (9 g) in water (12.5 mL) followed by a solution of 1-(4-chloro-phenyl)-cyclobutanecarboxylic acid (15 g) in isopropanol (150 mL) also in one portion. The resultant suspension was stirred at 65° C. for 30 minutes and then treated with a further aliquot of a solution of ammonium formate (9 g) in water (12.5 mL). After stirring at 65° C. for a further 4.5 hours the reaction mixture was filtered through Hyflo and the filter pad was washed three times with isopropanol (75 mL). The combined filtrate and washings were evaporated. The solid obtained after standing at room temperature for 3 days was treated with ethyl acetate (350 mL) and water (150 mL) and the organic phase was separated, then dried over magnesium sulfate and then evaporated to give the title compound (9.25 g) as a white solid. LC-MS: RT=3.08 minutes, MS(ES+): very weak 177(M+H)+.

Workup

  1. filtrationwas filtered through Hyflo
  2. washthe filter pad was washed three times with isopropanol (75 mL)
  3. customThe combined filtrate and washings were evaporated
  4. customThe solid obtained
  5. waitafter standing at room temperature for 3 days
  6. customthe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-d276a7308cd242c3b025f2a09e50c4fe
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

Loading…