Allyl Alcohol → HCID 21288544, compound

HRID 868387Notes

Reaction equation

HRID 868387 reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Cl)=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:15]([OH:18])[CH:16]=[CH2:17]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:15]([O:18][CH2:11][C:10]1[CH:13]=[CH:14][C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])=[CH:8][CH:9]=1)[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 14798Sodium HydroxideHCID 88198Benzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-

Product 1

HCID 21288544HCID 21288544, compound

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Procedure

88 g (1.1 mol) of 50% sodium hydroxide solution are treated with 4.6 g (0.016 mol) of tetrabutylammonium chloride. At a temperature of 35° C. there is added dropwise within about 20 minutes while stirring well a mixture of 182.5 g (1.0 mol) of p-tert-butylbenzyl chloride and 61.5 g (1.06 mol) of allyl alcohol. The temperature is held at <70° C., which is accomplished if necessary by slight cooling. The mixture is stirred well at 70° C. for a further 12 hours. After cooling, the reaction mixture is washed twice with dilute hydrochloric acid. 204 g of practically pure p-tert-butylbenzyl allyl ether are obtained. The substance can be used without distillation for the next step.

Workup

  1. additionAt a temperature of 35° C. there is added dropwise within about 20 minutes
  2. customis held at <70° C.
  3. stirringThe mixture is stirred well at 70° C. for a further 12 hours
  4. temperatureAfter cooling
  5. washthe reaction mixture is washed twice with dilute hydrochloric acid

Sources & evidence

ORD record
ord-4f5d3652f7be4e73879c1479d5bec6f3
Source dataset
uspto-grants-1988_10
Patent number
US04778934

Reaction notes

Loading…