Phenol → HCID 18979235, compound

HRID 2393184Notes

Reaction equation

HRID 2393184 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22].[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH2:31](Cl)Cl>>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH:16]([C:27]1[CH:28]=[CH:29][C:24]([OH:30])=[CH:25][CH:26]=1)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:31])=[O:22]

Participants

4

Reactant 3

HCID 996PhenolHCID 6344DichloromethaneHCID 536355006-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)hex-5-enoic acid

Product 1

HCID 18979235HCID 18979235, compound

Procedure

To a solution of 25.6 g of 6-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-5-hexenoic acid and 23 g of phenol in 250 ml of methylene chloride was added 20.6 ml of boron trifluoride diethyl ether complex at 0° C. The solution was stirred at room temperature for 24 hours and poured into ice-water. The organic layer was separated, washed, dried, and evaporated. The residue was dissolved in 400 ml of methanol and 8 ml of c.HCl . The solution was heated at 60° C. for 1 hour, and the solvent was removed by evaporation. The residue was purified with column chromatography over silica gel using n-hexane/ethyl acetate (7/1-2/1) as an eluent to give 20.5 g of the titled compound as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed
  3. customdried
  4. customevaporated
  5. dissolutionThe residue was dissolved in 400 ml of methanol
  6. temperatureThe solution was heated at 60° C. for 1 hour
  7. customthe solvent was removed by evaporation
  8. customThe residue was purified with column chromatography over silica gel

Sources & evidence

ORD record
ord-e6322830f5f8400d82a14c1a9381928c
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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