Hydrochloric Acid → HCID 19880033, compound

HRID 1885127Notes

Reaction equation

HRID 1885127 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[OH-:9].[K+].S([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)([O-])(=O)=O.Cl>O.C(O)C.CO>[CH2:4]([O:9][CH:18]([CH3:19])[CH2:20][CH2:21][CH2:15][CH2:16][CH2:17][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[CH2:3][CH2:1][CH2:8][CH3:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 14797Potassium HydroxideHCID 85570p-Toluenesulfonate

Product 1

HCID 19880033HCID 19880033, compoundYield 66.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2.3 g of hydroquinone, 0.94 g of 85% KOH, 4 ml of methanol and 20 ml of ethanol were stirred at 50°-53° C., and 4.36 g of the above tosylate was dropped in 1 hour. After the addition, the mixture was stirred for 2 hours at 60°-65° C. and for 5 hours at 76°-78° C. After the reaction, the mixture was poured into cold water, acidified to pH 1 with 6N-hydrochloric acid and extracted with hexane. After being washed with water, the extract was dried with anhydrous MgSO4, and the solvent was distilled off. The product was further purified by silica gel column chromatography (hexane/ethyl acetate=10/3) to obtain 2.05 g of 4-(6-pentyloxyheptyloxy)phenol.

Workup

  1. additionAfter the addition
  2. customAfter the reaction
  3. extractionextracted with hexane
  4. washAfter being washed with water
  5. dry with materialthe extract was dried with anhydrous MgSO4
  6. distillationthe solvent was distilled off
  7. customThe product was further purified by silica gel column chromatography (hexane/ethyl acetate=10/3)

Sources & evidence

ORD record
ord-1bca3809bd46493f9ad943e7390b2b2d
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

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