Hydroquinone → 4-(6-(2-Tetrahydropyranyl)oxyhexyloxy)phenol

HRID 28312

Reaction equation

HRID 28312 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1.[C:15]1([CH:22]=[CH:21][C:19]([OH:20])=[CH:18][CH:17]=1)[OH:16].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CS(C)=O>[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:16][C:15]1[CH:22]=[CH:21][C:19]([OH:20])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 3298032-(6-Chlorohexyloxy)tetrahydro-2H-pyran

Product 1

HCID 178385764-(6-(2-Tetrahydropyranyl)oxyhexyloxy)phenolYield 82.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 10 g of 2-(6-chlorohexyloxy)tetrahydropyrane, 25 g of hydroquinone, 31 g of potassiumcarbonate, 0.752 g of potassiumiodide and 250 ml of dimethylsulfoxide was allowed to react for 4 days at 80° C. Subsequently, the reaction mixture was cooled to room temperature and after addition of water extracted with ether. The organic phase was then dried over sodium sulphate, filtered and concentrated to dryness. Chromatography on silica with 10% ethylacetate in toluene gave 11 g of product as a yellowish oil.

Workup

  1. customto react for 4 days at 80° C
  2. extractionextracted with ether
  3. dry with materialThe organic phase was then dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7f83b244a5014c8fbe2f48fda79a83a5
Source dataset
uspto-grants-2008_09
Patent number
US07419620B2

Linked notes

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