Ethanol → HCID 20276905, compound

HRID 1248554Notes

Reaction equation

HRID 1248554 reaction equation
[CH:1]#[C:2][CH2:3][OH:4].Cl.NO.[OH-].[K+].Cl[C:11]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12]C.[CH2:19](O)C>>[CH3:18][C:15]([CH3:16])([CH3:17])[CH2:14][C:11](=[CH2:12])[CH2:19][C:1]#[C:2][CH2:3][OH:4]

Participants

6

Reactant 5

HCID 702EthanolHCID 7859Propargyl alcoholHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86740157HCID 86740157, compound

Product 1

HCID 20276905HCID 20276905, compoundYield 45%

Procedure

11.2 g (0.2M) of prop-1-yn-3-ol, 1.0 g of hydroxylamine hydrochloride and 1.4 g of Cu2Cl2 have been added to a solution of 14.6 g of KOH (0.26M) in 80 ml of ethanol. The resulting mixture has been stirred vigorously for 10 minutes, then 87.9 g of 2-chloro-methyl-4,4-dimethyl-pent-1-ene of technical grade (0.4M of pure product) were added thereto. The addition was exothermic and the mixture was kept at 25°-32° during the whole operation (45 min), while the stirring was maintained overnight. The resulting reaction mixture was taken up with 30°-50° petrol ether, washed successively with water, 10% HCl and with water again until neutrality. After drying and evaporation, the obtained residue was distilled to give 16.6 g of 5-(2,2-dimethyl-propyl)-5-hexen-2-yn-1-ol (yield 45%).

Workup

  1. additionThe addition
  2. customwas kept at 25°-32° during the whole operation (45 min), while the stirring
  3. temperaturewas maintained overnight
  4. customThe resulting reaction mixture
  5. customwas taken up with 30°-50°
  6. washwashed successively with water, 10% HCl and with water again until neutrality
  7. customAfter drying
  8. customevaporation
  9. distillationthe obtained residue was distilled

Sources & evidence

ORD record
ord-15b4ab617f094454af383129535c3b4f
Source dataset
uspto-grants-1985_06
Patent number
US04525298

Reaction notes

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