4-Methoxyphenol → HCID 19894527, compound

HRID 892998Notes

Reaction equation

HRID 892998 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[C:10](=O)([O-])[O-].[K+].[K+].ClC[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23]>CS(C)=O>[OH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 19894527HCID 19894527, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-methoxyphenol (8.7 g), potassium carbonate (9.7 g), 6-chlorohexanol (9.55 g) and DMSO (80 ml) is heated at 120° for 18 hr. Most all of the DMSO is removed at reduced pressure and the residue distributed between ether (400 ml) and water (400 ml). The ether phase is washed with water, saline, dried over sodium sulfate and the solvent removed at reduced pressure to give a residue which is crystallized from ether to give the title compound, m.p. 63°-64°; MS (m/e) 224 (M+).

Workup

  1. temperatureis heated at 120° for 18 hr
  2. customMost all of the DMSO is removed at reduced pressure
  3. washThe ether phase is washed with water, saline
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed at reduced pressure
  6. customto give a residue which
  7. customis crystallized from ether

Sources & evidence

ORD record
ord-ec13f0f820524a1eacb056511bd5fd3d
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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