Acetaldehyde → 1-(3,3-Dimethyl-2-norbornyl)-2-propanone

HRID 972895

Reaction equation

HRID 972895 reaction equation
[CH:1]12[CH2:10][CH:7]([CH2:8][CH2:9]1)[C:5](=[CH2:6])[C:2]2([CH3:4])[CH3:3].[CH:11](=[O:13])[CH3:12].CC1C=CC(C)=CC=1C>>[CH3:3][C:2]1([CH3:4])[CH:1]2[CH2:10][CH:7]([CH2:8][CH2:9]2)[CH:5]1[CH2:6][C:11](=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 6616CampheneHCID 72471,2,4-Trimethylbenzene

Product 1

HCID 203481821-(3,3-Dimethyl-2-norbornyl)-2-propanoneYield 40.5%

Procedure

A 1 liter water jacketed photochemical reaction vessel equipped with magnetic stirrer and pyrex immersion well is charged with 418 g camphene (807, Aldrich) and 372 g acetaldehyde and 30 g diacetyl (photochemical hydrogen abstractor). The mixture is irradiated with a 450 medium pressure mercury lamp (Hanovia) for 55 hours, during which time five 30 g portions of diacetyl are added at varying intervals. The reaction mixture is combined with 150 g of 1,2,4-trimethyl benzene and washed with water. The material is distilled without fractionation and then redistilled through a 5 foot Vigreux column to yield 224 g colorless product, b.p. 70°-72° (55 mm Hg).

Workup

  1. customA 1 liter water jacketed photochemical reaction vessel equipped with magnetic stirrer
  2. additionare added
  3. washwashed with water
  4. distillationThe material is distilled without fractionation
  5. distillationredistilled through a 5 foot Vigreux column

Sources & evidence

ORD record
ord-70536a79aaff4d7287ee5356048f634e
Source dataset
uspto-grants-1977_10
Patent number
US04053657

Linked notes

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