Tert-Butylhydroquinone → HCID 13050503, compound

HRID 1703357Notes

Reaction equation

HRID 1703357 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21]>CN(C)C=O>[CH3:3][C:1]([C:5]1[CH:11]=[C:10]([O:12][CH2:16][CH2:17][CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])[CH:9]=[CH:8][C:6]=1[O:7][CH2:16][CH2:17][CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 16043Tert-ButylhydroquinoneHCID 24758Sodium hydrideHCID 13050502Methyl 5-bromo-2,2-dimethylpentanoate

Product 1

HCID 13050503HCID 13050503, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.32 g of t-butylhydroquinone in 15 ml of dimethylformamide is added dropwise to a suspension of 2.4 g of 50% sodium hydride in 25 ml of dimethylformamide, and allowed to stir for 1/2 an hour at room temperature. 11.2 g of methyl 5-bromo-2,2-dimethylpentanoate is added followed by heating the mixture at 60°-70° C. for 6 hrs. Dimethylformamide is distilled off, the residue is poured into water and the organic material is extracted with ether. The ether extract is washed with water until neutral, dried over anhydrous magnesium sulfate and the ether is evaporated. The residue is purified by distillation yielding the product, dimethyl 5,5'-[[2-(1,1-dimethylethyl)1,4-phenylene]bis(oxy)]bis[2,2-dimethylpentanoate] b.p. 200° C. at 0.5 mm of Hg; yield 4 g.

Workup

  1. temperatureby heating the mixture at 60°-70° C. for 6 hrs
  2. distillationDimethylformamide is distilled off
  3. additionthe residue is poured into water
  4. extractionthe organic material is extracted with ether
  5. extractionThe ether extract
  6. washis washed with water until neutral,
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe ether is evaporated
  9. distillationThe residue is purified by distillation

Sources & evidence

ORD record
ord-094bb1270cf94c5abca47a9aba31f477
Source dataset
uspto-grants-1982_09
Patent number
US04351950

Reaction notes

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