Hydrochloric Acid → HCID 14896943, compound

HRID 2389335Notes

Reaction equation

HRID 2389335 reaction equation
C([Li])CCC.[CH2:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O:19]1[C:23](=[O:24])[CH2:22][CH2:21][C:20]1=[O:25].Cl>CCCCCC.C1COCC1.CCOC(C)=O>[O:24]=[C:23]([CH:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:22][CH2:21][C:20]([OH:25])=[O:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7580DiphenylmethaneHCID 7922Succinic anhydrideHCID 178418339Butyllithium

Product 1

HCID 14896943HCID 14896943, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.59M n-Butyllithium solution in n-hexane (25 mL) was added dropwise to a stirred solution of 1,1′-methylenedibenzene (6.73 g) in THF (75 mL) below 35° C. under N2 gas atmosphere. The reaction mixture was added dropwise to a solution of dihydrofuran-2,5-dione(2 g) in THF (50 mL) below 25° C. After stirring for 4 hours. 1M HCl aqueous solution (45 mL) and EtOAc were poured into the reaction mixture. The organic layer was separated and was washed with water and brine, and dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (DCM:MeOH). The desired fractions were collected and evaporated in vacuo to give 4-oxo-5,5-diphenylpentanoic acid (2.48 g) as a yellow solid.

Workup

  1. customThe organic layer was separated
  2. washwas washed with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (DCM:MeOH)
  7. customThe desired fractions were collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-9616337d18e24df4a4f0bcba46dc1d99
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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