Hydrochloric Acid → HCID 18790055, compound

HRID 1107131Notes

Reaction equation

HRID 1107131 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[C:20]1([O:28][CH3:29])[C:21](=[CH:24][CH:25]=[CH:26][CH:27]=1)[O:22][CH3:23].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[CH3:23][O:22][C:21]1[CH:24]=[C:25]([C:11](=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:26]=[CH:27][C:20]=1[O:28][CH3:29]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7043VeratroleHCID 16757Benzenepentanoic acidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18790055HCID 18790055, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-phenylvaleric acid (10 g, 56.1 mmol) in dichloromethane (70 mL) is added 2 M oxalyl chloride (33.5 mL, 67 mmol). The mixture is stirred at room temperature for 18 hours. The solvent is removed in vacuo. The residue is dissolved in dichloromethane (60 mL) and veratrole (11.6 g, 84 mmol) is added. The mixture is cooled in ice and aluminum chloride (7.4 g, 56.1 mmol) is added in portions over 10 minutes. The mixture is stirred for 3 hours warming to room temperature. The mixture is added to aqueous HCl and is extracted with dichloromethane. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo and the residue is chromatographed on silica gel (7:3 hexane:ethyl acetate) to give 1-(3,4-dimethoxyphenyl)-1-oxo-5-phenylpentane (5.5 g 33%), m.p. 56-8° C. 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.68-1.82 (m, 4H), 2.52-2.61 (t, 2H), 2.88-2.98 (t, 2H), 3.95 (s, 6H), 6.82-6.92 (m, 2H), 7.10-7.30 (m, 4H), 7.48-7.60 (m, 2H); MS (EI) m/e 298 (M+).

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in dichloromethane (60 mL)
  3. temperatureThe mixture is cooled in ice
  4. stirringThe mixture is stirred for 3 hours
  5. temperaturewarming to room temperature
  6. extractionis extracted with dichloromethane
  7. washThe organic layer is washed with water
  8. dry with materialis dried over MgSO4
  9. customThe solvent is removed in vacuo
  10. customthe residue is chromatographed on silica gel (7:3 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-74664d49acb54a0d82dfcd0c80e16409
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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