Guaiacol → Benzene, 1-methoxy-2-(2-propen-1-yloxy)-

HRID 654753Notes

Reaction equation

HRID 654753 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[CH:17]=[CH2:18]>CN(C)C=O.O>[CH2:16]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH:17]=[CH2:18]

Participants

6

Reactant 3

HCID 460GuaiacolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 77777Benzene, 1-methoxy-2-(2-propen-1-yloxy)-Yield 79.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

124 g of 2-methoxyphenol and 152 g of potassium carbonate in 500 ml of dimethylformamide are brought to 60° C. with stirring for 30 minutes. 127 g of allyl bromide are introduced and the reaction medium is then left at 60° C. for 1 hour. It is diluted with 2 l of water and extracted with ethyl ether and the organic phase is washed with sodium hydroxide. The organic phase is dried and the ether evaporated off. The product is then distilled at 115° C. and at 20 mmHg to obtain 129.6 g of the expected compound.

Workup

  1. customare brought to 60° C.
  2. waitthe reaction medium is then left at 60° C. for 1 hour
  3. extractionextracted with ethyl ether
  4. washthe organic phase is washed with sodium hydroxide
  5. customThe organic phase is dried
  6. customthe ether evaporated off
  7. distillationThe product is then distilled at 115° C. and at 20 mmHg

Sources & evidence

ORD record
ord-cadc97bd9bac48fb85200a6bbc548526
Source dataset
uspto-grants-1992_07
Patent number
US05134147

Reaction notes

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