Hydrochloric Acid → HCID 19757561, compound

HRID 1587263Notes

Reaction equation

HRID 1587263 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][Si:14]([CH2:17][CH2:18][CH2:19][CH3:20])([CH3:16])[CH3:15])(=O)=O)=CC=1.[C:22]1([CH:29]=[CH:28][C:26]([OH:27])=[CH:25][CH:24]=1)[OH:23].[OH-].[K+].Cl>O.C(O)C.CO>[CH2:17]([Si:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH2:11][O:23][C:22]1[CH:29]=[CH:28][C:26]([OH:27])=[CH:25][CH:24]=1)[CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 14797Potassium HydroxideHCID 19757560HCID 19757560, compound

Product 1

HCID 19757561HCID 19757561, compoundYield 50.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

The above-obtained 3-(butyldimethylsilyl)propyl p-toluenesulfonate was added dropwise in 45 min. to a mixture of 2.32 g (21.1 mM) of hydroquinone, 1.13 g (17.1 mM) of 85 %-potassium hydroxide, 6 ml of methanol and 30 ml of ethanol under stirring at 65° C., followed by stirring for 0.5 hour and further stirring for 6 hour at 80° C. After the reaction, the reaction mixture was poured into cold water, acidified with hydrochloric acid (pH≈2) and extracted with ethyl acetate, followed by washing with water and drying with anhydrous magnesium sulfate. The magnesium sulfate in the resultant mixture was filtered off and the filtrate was condensed into a solid, followed by purification by silica gel column chromatography (eluent: toluene) to obtain 2.05 g of 4-[3-(butyldimethylsilyl)propoxy]phenol (Yield: 50.6 %).

Workup

  1. stirringby stirring for 0.5 hour
  2. stirringfurther stirring for 6 hour at 80° C
  3. customAfter the reaction
  4. extractionextracted with ethyl acetate
  5. washby washing with water
  6. dry with materialdrying with anhydrous magnesium sulfate
  7. filtrationThe magnesium sulfate in the resultant mixture was filtered off
  8. customcondensed into a solid
  9. customfollowed by purification by silica gel column chromatography (eluent: toluene)

Sources & evidence

ORD record
ord-7fb995eaa5dd49e78960a2ebbc3b68d0
Source dataset
uspto-grants-1993_06
Patent number
US05217645

Reaction notes

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