Epichlorohydrin → HCID 12114671, compound

HRID 397598Notes

Reaction equation

HRID 397598 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22](C)[CH:21]=2)[C:10]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[CH2:28]([CH:30]1[O:32][CH2:31]1)Cl.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:28][CH:30]3[O:32][CH2:31]3)=[CH:24][CH:25]=2)[C:10]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 12114667HCID 12114667, compound

Product 1

HCID 12114671HCID 12114671, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (4-methoxyphenyl)-(3-methyl-4-hydroxyphenyl)-5,6,7,8-tetrahydronaphth-1-yl-methane (410 mg, 0.001 mol), epichlorohydrin (25 ml) and anhydrous K2CO3 (2.0 gm, 0.014 mol) was refluxed at 120° C. for 6 hrs, K2CO3 was filtered off and the filtrate was concentrated. The residue obtained was dissolved in ethyl acetate and washed with water, dried over sodium sulphate and concentrated to give an oil which was chromatographed over silica gel using hexane:chloroform as the eluent to give the title compound. Yield 388 mg (82.37%).

Workup

  1. filtrationK2CO3 was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue obtained
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customto give an oil which
  8. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-ea36be1bcf9d487eab3f3b6cbbd892d7
Source dataset
uspto-grants-2003_08
Patent number
US06610705B1

Reaction notes

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