Hydroquinone → HCID 14750504, compound

HRID 2351869Notes

Reaction equation

HRID 2351869 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][CH2:11][C:12]#[N:13].[OH-].[Na+].C1COCC1>CN(C=O)C.O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][C:12]#[N:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 8028TetrahydrofuranHCID 109633-ChloropropionitrileHCID 14798Sodium Hydroxide

Product 1

HCID 14750504HCID 14750504, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.43 g (0.013 mol) 1,4-dihydroxybenzene, 1.15 g (0.013 mol) 3-chloropropionitrile and 15 ml (2N, NaOH) in 15 ml DMF anmd 50 ml THF is stirred overnight at 60° C. bath temperature. The reaction mixture is poured into water and extracted with ether. The ether extract is washed with water, dried and concentrated to dryness under reduced pressure. The residue is passed through a silica gel column using hexane/ethylacetate (3:1) as eluent. Evaporation of eluent gives the desired product which is used directly in the next step.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washis washed with water
  4. customdried
  5. concentrationconcentrated to dryness under reduced pressure
  6. customEvaporation of eluent

Sources & evidence

ORD record
ord-531af64e75554ab7a7738f20e46d3a04
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

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