Epichlorohydrin → HCID 12114671, compound

HRID 397597Notes

Reaction equation

HRID 397597 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])=[CH:22][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.[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>>[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][CH2:27][CH:29]3[O:31][CH2:30]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

3

Reactant 2

HCID 7835EpichlorohydrinHCID 12114666(4-methoxyphenyl)-(4-hydroxyphenyl)-5,6,7,8-tetrahydronaphth-1-yl-methane

Product 1

HCID 12114671HCID 12114671, compound

Conditions

Temperature
110 °C

Procedure

A mixture of (4-methoxyphenyl)-(4-hydroxyphenyl)-5,6,7,8-tetrahydronaphth-1-yl-methane (450 mg, 0.0013 mol) anhydrous K2CO3 (2.8 gm, 1.44 mmol), epichlorohydrin (20 ml) was refluxed at 100-120° C. for 12 hrs. The reaction mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with water, dried over sodium sulphate and concentrated to give an oil. The oil was chromatographed over silica gel using 20% hexane:chloroform as the eluent to give the desired compound as an oil. Yield 410 mg (78.39%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe oil was chromatographed over silica gel using 20% hexane

Sources & evidence

ORD record
ord-49e1242a58454b34bf284aa0cd4a1a0f
Source dataset
uspto-grants-2003_08
Patent number
US06610705B1

Reaction notes

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