Formaldehyde → 3-[(dimethylamino)methyl]Benzenemethanol

HRID 2413164Notes

Reaction equation

HRID 2413164 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[CH2:5][N:6]([CH3:8])[CH3:7].[Mg].[CH2:13]=[O:14]>O1CCCC1>[CH3:7][N:6]([CH2:5][C:4]1[CH:3]=[C:2]([CH:11]=[CH:10][CH:9]=1)[CH2:13][OH:14])[CH3:8]

Participants

5

Reactant 3

HCID 712Formaldehyde2×HCID 4341665(3-BROMOBENZYL)DIMETHYLAMINEHCID 5462224Magnesium

Product 1

HCID 129520183-[(dimethylamino)methyl]BenzenemethanolYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Bromo-N,N-dimethylbenzylamine (21.4 g) was reacted with magnesium turnings (2.4 g) in dry tetrahydrofuran (75 ml). The mixture was cooled to 0° and gaseous formaldehyde (generated by heating 15 g paraformaldehyde in a stream of argon) was passed over the stirred solution. Tetrahydrofuran (25 ml) was added and the mixture was stirred at room temperature for 2.5 hours and acidified to pH 1. The mixture was extracted with aqueous 3N hydrochloric acid, and the aqueous extracts were made alkaline with aqueous sodium hydroxide and extracted with ether. The ether extracts were evaporated to give 3-(dimethylaminomethyl)benzyl alcohol (14.78 g, 78%).

Workup

  1. temperatureThe mixture was cooled to 0°
  2. extractionThe mixture was extracted with aqueous 3N hydrochloric acid
  3. extractionextracted with ether
  4. customThe ether extracts were evaporated

Sources & evidence

ORD record
ord-2d41ab2ae4414100b4679ce549b2957f
Source dataset
uspto-grants-1985_01
Patent number
US04496567

Reaction notes

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