Acetic Acid → HCID 15858476, compound

HRID 1418769Notes

Reaction equation

HRID 1418769 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[C:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH:22]([CH3:24])[CH3:23])[CH:15]=1)(O)[CH3:12].CC(O)=O.[H][H]>CCO>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[CH:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH:22]([CH3:24])[CH3:23])[CH:15]=1)[CH3:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 54537602HCID 54537602, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15858476HCID 15858476, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(2,6-dimethyl-4-methoxyphenyl)-1-(3-isopropyl-4-methoxyphenyl) ethanol (400 mg, 1.218 mmol) in 4.4 mL of 9% (v/v) AcOH in EtOH containing 10% Pd/C (40 mg) was hydrogenated at 1 atm at room temperature. When hydrogen uptake was complete (12 hours), the catalyst was filtered off and the filtrate was diluted with 50 mL of ether, washed with sat. NaHCO3 solution (3×10 mL), water (30 mL) and brine (3×10 mL). The solvent was evaporated to yield 300 mg (0.96 mmol, 79%) of 1-(2,6-dimethyl-4-methoxyphenyl)-1-(3-isopropyl-4-methoxyphenyl) ethane as an oil. This material was used in the next step without further purification; 1HNMR (CDCl3) & 1.16 (dd, 6H), 1.63 (d, 3H), 2.12 (s, 6H), 3.27 (heptet, 1H), 3.81 (s, 6H), 4.54 (q, 1H), 6.54 (s, 2H), 6.75 (d, 1H), 6.88 (d, 1H), 7.04 (s, 1H).

Workup

  1. customwas hydrogenated at 1 atm at room temperature
  2. custom(12 hours)
  3. filtrationthe catalyst was filtered off
  4. additionthe filtrate was diluted with 50 mL of ether
  5. washwashed with sat. NaHCO3 solution (3×10 mL), water (30 mL) and brine (3×10 mL)
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-60efe64616994eefb8c468aec61bf643
Source dataset
uspto-grants-1999_03
Patent number
US05883294

Reaction notes

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