Epichlorohydrin → 1,2,3,4-Tetrahydro-5-[2,3-epoxy-propoxy]-2-naphthol

HRID 1576691Notes

Reaction equation

HRID 1576691 reaction equation
[C:1]1([OH:12])[C:10]2[CH2:9][CH2:8][CH:7]([OH:11])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl>CO>[O:20]1[CH2:19][CH:18]1[CH2:16][O:12][C:1]1[CH:2]=[CH:3][CH:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH:7]([OH:11])[CH2:6]2

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 10942334Sodium MethoxideHCID 124457385,6,7,8-Tetrahydronaphthalene-1,6-diol

Product 1

HCID 124457671,2,3,4-Tetrahydro-5-[2,3-epoxy-propoxy]-2-naphthol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.46 g. (0.015 mole) of 5,6,7,8-tetrahydro-1,6-naphthalenediol and 810 mg. (0.015 mole) of sodium methoxide in 30 ml. of methanol is prepared under nitrogen and the solvent removed in vacuo. The resulting foam is stirred overnight with 20 ml. of dimethylsulfoxide and 1.40 g. (0.015 mole) of epichlorohydrin, poured into 200 ml. of water and extracted with four 125 ml. portions of ether. Drying and solvent removal gives 3.06 g. of oil which is purified by chromatography on silica gel (75 g.). Elution with hexane-chloroform mixtures gives a total of 1.56 g. (49%) of material with one spot on TLC.

Workup

  1. customthe solvent removed in vacuo
  2. extractionof water and extracted with four 125 ml
  3. customDrying
  4. customsolvent removal
  5. customgives 3.06 g
  6. customof oil which is purified by chromatography on silica gel (75 g.)
  7. washElution with hexane-chloroform mixtures
  8. customgives a total of 1.56 g

Sources & evidence

ORD record
ord-473e602699f244bcadb8adb49e4cc0f5
Source dataset
uspto-grants-1976_09
Patent number
US03982021

Reaction notes

Loading…