Hexane → 2-[2-(3-methoxyphenyl)ethyl]benzoic Acid

HRID 840500Notes

Reaction equation

HRID 840500 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH:6]=[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[O:8]1.C([O-])=O.[NH4+].C(N(CC)CC)C.CCCCCC>C1COCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]([OH:16])=[O:8])[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 2723923Ammonium formateHCID 544728733-[(3-Methoxyphenyl)methylidene]-2-benzofuran-1(3H)-one

Product 1

HCID 104675922-[2-(3-methoxyphenyl)ethyl]benzoic AcidYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 15.6 g of 1 (62 mmol) in 300 ml of THF was added 30 g of 10% Pd-C, 40 g of ammonium formate and 17.2 ml of triethyl amine. The reaction mixture was heated at 70° C. for 6 hours and filtered. The filtrate was concentrated and redissolved in 500 ml of ethyl acetate and washed with 2×150 ml of 3% aqueous HCl and 2×100 ml of brine. The organic layer was concentrated and triturated with 1:1 ethyl acetate:hexane to give 8 g (31.2 mmol, 51%) of 2.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. dissolutionredissolved in 500 ml of ethyl acetate
  4. washwashed with 2×150 ml of 3% aqueous HCl and 2×100 ml of brine
  5. concentrationThe organic layer was concentrated
  6. customtriturated with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-2f6dcd3390374de0bc6186dcc5b4bbf7
Source dataset
uspto-grants-2002_04
Patent number
US06368814B1

Reaction notes

Loading…