Phenol → HCID 69595408, compound

HRID 724463Notes

Reaction equation

HRID 724463 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+].C1(O)C=CC=CC=1.Cl[CH2:24][CH2:25][O:26][CH2:27][CH2:28]Cl>C(O)C.O>[CH2:25]([O:26][CH2:27][CH2:28][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])[CH3:24]

Participants

7

Reactant 4

HCID 996PhenolHCID 8115Bis(2-chloroethyl) etherHCID 14798Sodium HydroxideHCID 728562,6-Di(prop-2-en-1-yl)phenol

Product 1

HCID 69595408HCID 69595408, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,6-Diallylphenol (5.2 g, 0.03 mol) was diluted with 95% ethanol (50 ml). Sodium hydroxide (1.4 gm, 0.03 mol) was added to the phenol solution followed by 2-chloroethylether (3.8 gm, 0.035 mol). The reaction mixture was refluxed for 48 hrs, cooled, diluted with water, extracted with hexane and dried over MgSO4. Filtration of the MgSO4 and evaporation of the hexane gave 5.1 g of 2,6-diallylphenyl ethoxyethyl ether. MS m/z 246 (M+ calcd for C16H22O2=246). H NMR (300 MHz, CDCl3) d 1.30 (3, t, CH3), 3.40–3.55 (4, m, CH2 allyl), 3.65–3.75 (2,q, OCH2 methyl), 3.80 (q, 2, OCH2), 4.00(q, 2, OCH2), 5.05–5.25 (m, 4, CH2 vinyl), 5.90–6.20 (m, 2, CH vinyl), 7.05–7.20 (m, 4, CH2 vinyl), 7.05–7.20 (m, 3, aromatic). Oxidation of the product as described in Example 1 gave 2,6-di-(2,3-epoxypropyl)phenyl ethoxyethyl ether as an oil. MS m/z 278 (M+ calcd for C16H22O4=278). H NMR (300 MHz, CDCl3) d 1.25 (t, 3, CH30, 2.65–2.85 (m, 4, epoxypropyl CH2), 2.90–3.15 (m, 4, epoxypropyl CH2), 3.21–3.35(m, 2, epoxypropyl CH), 3.65 (q, 2, OCH2), 3.80 (q, 2, OCH2), 4.00 (q, 2, OCH2), 5.33 (s, 3, OCH3), 7.05–7.33 (m, 3, aromatic).

Workup

  1. temperatureThe reaction mixture was refluxed for 48 hrs
  2. temperaturecooled
  3. extractionextracted with hexane
  4. dry with materialdried over MgSO4
  5. filtrationFiltration of the MgSO4 and evaporation of the hexane

Sources & evidence

ORD record
ord-9a6db1f014db40df945d2e8ac5b97bc4
Source dataset
uspto-grants-2006_11
Patent number
US07141684B2

Reaction notes

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