Toluene → HCID 131710960, compound

HRID 461093Notes

Reaction equation

HRID 461093 reaction equation
[C:1]12([C:8]3[CH:13]=[C:12]([CH3:14])[C:11]([CH3:15])=[CH:10][C:9]=3[OH:16])[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.C1(C)C=CC=CC=1.[Na].[CH2:25]([CH:27]1[O:29][CH2:28]1)Cl>O.CCOCC>[C:1]12([C:8]3[CH:13]=[C:12]([CH3:14])[C:11]([CH3:15])=[CH:10][C:9]=3[O:16][CH2:25][CH:27]3[O:29][CH2:28]3)[CH2:7][CH:4]([CH2:3][CH2:2]1)[CH2:5][CH2:6]2

Participants

7

Reactant 4

HCID 1140TolueneHCID 7835EpichlorohydrinHCID 5360545SodiumHCID 131710961HCID 131710961, compound

Product 1

HCID 131710960HCID 131710960, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

108g (0.5 mole) of 2-norbornyl-4,5-dimethyl phenol, 600 cm3 anhydrous toluene and 11.5g (0.5 mole) sodium are introduced into a three-necked flask supplied with a nitrogen stream. The reaction mixture is refluxed for 4 hours, the solvent is then removed and the residue taken up in 500 cm3 tetrahydrofuran. 39.4 cm3 (0.5 mole) epichlorohydrin are added and the mixture is heated under reflux for 8 hours. One extracts with ether, washes the ethereal phase with water, dries and evaporates the solvent. 123.6g of 1-(2'-norbornyl-4',5'-dimethyl phenoxy) 2,3-epoxypropane are obtained in the form of oil. 27.2g (0.1 mole) of the preceding product are dissolved in 100 cm3 isopropylamine. After 5 days contact, the excess amine is evaporated under reduced pressure and extracted with ether. After washing with water and drying, the ether is evaporated and the residue taken up in chloroform. One precipitates by adding gaseous hydrochloric acid. By crystallisation in methylethyl ketone, 20g of pure product are obtained. M.Pt. 183°-185° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. customthe solvent is then removed
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 8 hours
  5. customevaporates the solvent

Sources & evidence

ORD record
ord-e33553c2536b4dee80a44fdce0c95198
Source dataset
uspto-grants-1977_12
Patent number
US04061777

Reaction notes

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