Epichlorohydrin → HCID 13157038, compound

HRID 964010Notes

Reaction equation

HRID 964010 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[OH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[OH:17].[OH-].[K+]>O>[O:6]1[CH:3]([CH2:4][OH:5])[CH2:1][O:17][C:8]2[CH:9]=[CH:10][C:11]3[C:16]([C:7]1=2)=[CH:15][CH:14]=[CH:13][CH:12]=3

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 113181,2-DihydroxynaphthaleneHCID 14797Potassium Hydroxide

Product 1

HCID 13157038HCID 13157038, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Epichlorohydrin (2.32 g) was added dropwise to a stirred solution of 1,2-dihydroxynaphthalene (4.0 g) and potassium hydroxide (4.0 g) in water (32 ml) and the resulting mixture stirred at 60°-80° C. for 2.5 hours then poured into water (100 ml). The product was extracted into ether (6×100 ml), a small volume of methanol being added to aid solubility. The combined extracts were washed with aqueous sodium hydroxide solution (1M), then water, and dried over magnesium sulphate. The solvent was removed in vacuo to give crude 1-(naphtho[1,2-b]dioxan-2-yl)methanol (4.0 g) as a dark oil which was used without further purification.

Workup

  1. extractionThe product was extracted into ether (6×100 ml)
  2. additiona small volume of methanol being added
  3. washThe combined extracts were washed with aqueous sodium hydroxide solution (1M)
  4. dry with materialwater, and dried over magnesium sulphate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bf249c08c4b249578a1c3b95f839accf
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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