Guaiacol → ((o-Methoxyphenoxy)methyl)oxirane

HRID 1532990Notes

Reaction equation

HRID 1532990 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].CC(C)([O-])C.[K+].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl.C1OCCOCCOCCOCCOCCOC1>C(O)(C)(C)C.O>[O:20]1[CH2:19][CH:18]1[CH2:16][O:3][C:2]1[CH:4]=[CH:5][CH:6]=[CH:7][C:1]=1[O:8][CH3:9]

Participants

7

Reactant 4

HCID 460GuaiacolHCID 7835EpichlorohydrinHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxide

Product 1

HCID 98357((o-Methoxyphenoxy)methyl)oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

Guaiacol (8.6 g, 69 mmol), potassium t-butoxide (7.8 g, 69 mmol), epichlorohydrin (19.3 g, 209 mmol), and 18-crown-6 (0.8 g) were mixed in t-butanol (100 ml) and heated to 50° C. for 2 h. Water was added and the product was extracted with two portions of dichlorometane. Washing with water, twice, was followed by drying and evaporation. Quantitative yield.

Workup

  1. extractionthe product was extracted with two portions of dichlorometane
  2. washWashing with water
  3. customby drying
  4. customevaporation

Sources & evidence

ORD record
ord-c363d1a1917e46ec87589c84bb7744e1
Source dataset
uspto-grants-2001_03
Patent number
US06207662B1

Reaction notes

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