Hydroquinone → HCID 20362369, compound

HRID 1729771Notes

Reaction equation

HRID 1729771 reaction equation
[CH2:1]=[CH:2][CH:3]([OH:11])[CH2:4][CH2:5][CH2:6][CH:7]([OH:10])[CH2:8][CH3:9].C1(C=CC(O)=CC=1)O>ClCCCl.[O-2].[O-2].[Mn+4]>[OH:11][CH:3]([CH2:2][CH3:1])[CH2:4][CH2:5][CH2:6][C:7](=[O:10])[CH:8]=[CH2:9]

Participants

5

Reactant 2

HCID 785HydroquinoneHCID 22245625HCID 22245625, compound

Product 1

HCID 20362369HCID 20362369, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 25 grams of 1-nonene-3,7-diol in 1,250 milliliters of 1,2-dichloroethane was added 0.25 gram of hydroquinone and 300 grams of manganese dioxide. The resulting slurry was stirred vigorously for 1 hour without heating, during which time the reaction temperature rose to about 30°C. The resulting reaction mixture was filtered and the manganese dioxide filter cake was washed thoroughly with 500 milliliters of 1,2-dichloroethane. The combined filtrates were evaporated in vacuo at 40°C. to yield 17.3 grams of 7-hydroxy-1-nonen-3-one. This compound is reacted with hydrogen chloride to produce 1-chloro-7-hydroxynonan-3-one, with dimethylamine to produce 1-(N,N-dimethylamino)-7-hydroxy-nonan-3-one, with water to produce 1,7-dihydroxynonan-3-one, or with ethanol to produce 1-ethoxy-7-hdyroxynonan-3-one.

Workup

  1. temperaturewithout heating, during which time the reaction temperature
  2. customrose to about 30°C
  3. customThe resulting reaction mixture
  4. filtrationwas filtered
  5. filtrationthe manganese dioxide filter cake
  6. washwas washed thoroughly with 500 milliliters of 1,2-dichloroethane
  7. customThe combined filtrates were evaporated in vacuo at 40°C.

Sources & evidence

ORD record
ord-8c620729a45648dc8a25a3ff6f11225b
Source dataset
uspto-grants-1976_11
Patent number
US03989724

Reaction notes

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