Formaldehyde → 2,6-Diethyl-4-methylbenzyl alcohol

HRID 385239Notes

Reaction equation

HRID 385239 reaction equation
[CH2:1]=[O:2].[CH2:3]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:6]=1[Mg]Br)[CH3:4].BrC1C(CC)=CC(C)=CC=1CC.[Mg]>C1COCC1>[CH2:3]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:6]=1[CH2:1][OH:2])[CH3:4]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5462224MagnesiumHCID 115794912-Bromo-1,3-diethyl-5-methylbenzeneHCID 178436244HCID 178436244, compound

Product 1

HCID 667075402,6-Diethyl-4-methylbenzyl alcoholYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Over a period of 30 min, gaseous formaldehyde (generated from 5.56 g of paraformaldehyde) is introduced with stirring into a solution of 2,6-diethyl-4-methylphenylmagnesium bromide, prepared from 12.40 g (54.6 mmol) of 1-bromo-2,6-diethyl-4-methylbenzene and 1.47 g (60.65 mmol) of magnesium turnings in 50 ml of THF, and the mixture is then stirred at room temperature for another 2 h. Distillative removal of the solvent and chromatography on silica gel (see above) gives 6.88 g (71%) of 2,6-diethyl-4-methylbenzyl alcohol.

Workup

  1. customDistillative removal of the solvent and chromatography on silica gel (see above)

Sources & evidence

ORD record
ord-c31da7488e184db396b4480431eb0d6a
Source dataset
uspto-grants-2013_02
Patent number
US08367873B2

Reaction notes

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