Hydroquinone → HCID 20383997, compound

HRID 1447510Notes

Reaction equation

HRID 1447510 reaction equation
[CH3:1]/[CH:2]=[C:3](/[CH:5]=[CH:6]/[CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[CH:11]([CH:13]=C)=[O:12].[C:15]1(C=CC(O)=CC=1)O>>[CH3:4][C:3]1[CH:2]([CH3:15])[CH2:1][CH:13]([CH:11]=[O:12])[CH:6]([CH:7]=[C:8]([CH3:10])[CH3:9])[CH:5]=1

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 7847AcroleinHCID 53688212,4,6-Octatriene, 2,6-dimethyl-, (4E,6E)-

Product 1

HCID 20383997HCID 20383997, compoundYield 66%

Procedure

408 g of allo-ocimene (85% 4E 6Z, 15% 4E 6E) and 202 g of acrolein were placed in a stainless steel vessel which is equipped to withstand a high internal pressure at elevated temperatures. 1 gm of hydroquinone, a polymerisation inhibitor, was added. The air in the vessel was displaced with nitrogen and the vessel closed. The temperature was raised to 145°-150° C. and maintained in the range for 7.5 hours. The maximum pressure recorded was 105 psi. The reaction mixture was then distilled and a mixture of four aldehydes collected which represented a 66% yield of the desired product. The percentages of adducts were A 4%, B 11%, C 74% and D 11% where the letters A, B, C, D represent the isomers denoted as such in Example 1.

Workup

  1. customwhich is equipped
  2. customthe vessel closed
  3. temperatureThe temperature was raised to 145°-150° C.
  4. temperaturemaintained in the range for 7.5 hours
  5. distillationThe reaction mixture was then distilled
  6. additiona mixture of four aldehydes
  7. customcollected which

Sources & evidence

ORD record
ord-e1104e23477b43638d9012f38bbf5d5d
Source dataset
uspto-grants-1979_12
Patent number
US04177170

Reaction notes

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