1,3-Cyclohexanedione → HCID 20305130, compound

HRID 866676Notes

Reaction equation

HRID 866676 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Cl.[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]1.[OH-].[K+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][CH:14]1[C:15](=[O:19])[CH2:16][CH2:17][CH2:18][C:13]1=[O:20]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 14797Potassium HydroxideHCID 123739901-(Chloromethyl)-2-(3-chloropropyl)benzene

Product 1

HCID 20305130HCID 20305130, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 155 g (0.75 mol) of 2-(3-chloropropyl)benzyl chloride 2 [Page, et al., J. Amer. Chem. Soc. 75:2053 (1953)], 91 g (0.81 mol) of 1,3-cyclohexanedione 1 [Aldrich Chem. Co. 10,160-5; Beilstein 7, 554], and 47 g of 85% KOH in 400 ml of methanol was refluxed 16 hours. After concentrating, the residue was partitioned between benzene and dilute aqueous NaOH solution. Acidification of the aqueous phase gave a solid that was recrystallized from ethyl acetate to give 34 g of the dione 3, mp 143°-145° C.

Workup

  1. concentrationAfter concentrating
  2. customthe residue was partitioned between benzene and dilute aqueous NaOH solution
  3. customAcidification of the aqueous phase gave a solid
  4. customthat was recrystallized from ethyl acetate
  5. customto give 34 g of the dione 3, mp 143°-145° C.

Sources & evidence

ORD record
ord-f91be6d9c12947b199dae5e82ea75ca7
Source dataset
uspto-grants-1978_07
Patent number
US04100353

Reaction notes

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