Allyl bromide → HCID 57242164, compound

HRID 566857Notes

Reaction equation

HRID 566857 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([CH3:8])[CH2:5][CH2:4][CH:3]1[CH:9]=[O:10].[CH2:12](Br)[CH:13]=[CH2:14].[NH4+].[Cl-]>CCOCC>[CH3:11][C:2]1([CH3:1])[CH2:7][CH:6]([CH3:8])[CH2:5][CH2:4][CH:3]1[C:9](=[O:10])[CH:12]=[CH:13][CH3:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 212637402,2,4-Trimethyl-1-cyclohexanecarbaldehyde

Product 1

HCID 57242164HCID 57242164, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2,2,4-Trimethyl-1-cyclohexanecarbaldehyde (11 g, 72 mmole) in ether (100 ml) was added dropwise with stirring to a Grignard compound prepared from Mg (2.3 g) and allylbromide (10 g) in ether and refluxed for 2 h. After cooling, the mixture was hydrolyzed with NH4Cl-solution, then distilled at a bath temperature of 150°/0.5 hPa, to obtain 11.3 g (80%) of the desired product as a 2:1 mixture of 2 isomers.

Workup

  1. temperaturerefluxed for 2 h
  2. temperatureAfter cooling
  3. distillationdistilled at a bath temperature of 150°/0.5 hPa

Sources & evidence

ORD record
ord-f0f38d8eae4f4a478dc83ed23c8fc1bf
Source dataset
uspto-grants-2001_01
Patent number
US06177400B1

Reaction notes

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