Benzyl Chloride → HCID 21880806, compound

HRID 724464Notes

Reaction equation

HRID 724464 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH:11]=[CH2:12])[C:5]=1[OH:13])[CH:2]=[CH2:3].[OH-].[Na+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO>[CH2:16]([O:13][C:5]1[C:4]([CH2:1][CH:2]=[CH2:3])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:10][CH:11]=[CH2:12])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 728562,6-Di(prop-2-en-1-yl)phenol

Product 1

HCID 21880806HCID 21880806, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,6-Diallylphenol (3.48 gm, 0.025 mol) was diluted with methanol (50 ml) and sodium hydroxide (0.8 gm 0.02 mol) was added to the solution followed by the benzyl chloride (3.60 gm, 0.2 mol.). The solution was refluxed for 2 hr, cooled, poured onto water and extracted with hexane. After washing with water and dilute sodium hydroxide, the organic layer was dried over MgSO4, filtered and evaporated to give 2,6-diallylphenyl benzyl ether. MS m/z 264 (M+ calcd for C19H20O=264). H NMR (300 MHz, CDCL3) d 3.45–3.55 (d, 4, CH2 allyl), 4.85 (s, 2, CH2 benzyl), 5.05–5.20 (m, 4, CH2 vinyl), 5.96–6.15 (m, 2, CH vinyl), 7.10–7.25 (m, 3, aromatic), 7.35–7.70 (m, 5, aromatic). Oxidation of the product as described in Example 1 gave 2,6-di(2,3-epoxyypropyl) phenyl benzyl ether as an oil. MS m/z 296 (M+ calcd for C+H20O3=296). H NMR (300 MHz, CDCl3) d 2.60–2.70 (m, 2, CH2 epoxypropyl), 2.75–3.10 (m, 6, CH2 epoxypropyl), 2.31–2.46 (m, 2, CH2 epoxypropyl), 4.75 (s, 2, CH2O), 7.10–7.25 (m, 1, aromatic) 7.45–7.60 (m, 2, aromatic), 7.60–8.15 (m, 5, aromatic).

Workup

  1. additionwas added to the solution
  2. temperatureThe solution was refluxed for 2 hr
  3. temperaturecooled
  4. additionpoured onto water
  5. extractionextracted with hexane
  6. washAfter washing with water and dilute sodium hydroxide
  7. dry with materialthe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-8ffba633edeb4cb7a5d7ed32e93ea6c5
Source dataset
uspto-grants-2006_11
Patent number
US07141684B2

Reaction notes

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