Tert-Butylamine → 2-Chloro-α-[[(1,1-dimethylethyl)amino]methyl]-5-hydroxybenzenemethanol

HRID 328817Notes

Reaction equation

HRID 328817 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([CH:11]=O)=[O:10].[C:13]([NH2:17])([CH3:16])([CH3:15])[CH3:14].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:9]([OH:10])[CH2:11][NH:17][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 4311764Sodium borohydrideHCID 12463890HCID 12463890, compound

Product 1

HCID 124639052-Chloro-α-[[(1,1-dimethylethyl)amino]methyl]-5-hydroxybenzenemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-chloro-5-hydroxyphenylglyoxal (1.85 g) in methanol (37 ml) was added a solution of tert-butylamine (3.65 g) in methanol under cooling, further the sodium borohydride (0.57 g) was added in small portions, and the reaction mixture was stirred for 3 hours. The reaction mixture was evaporated and the residue acidified with 10% HCl, and washed with ether. The aqueous layer was made alkaline with K2CO3, and extracted with ether. The extract was dried with Na2SO4 and evaporated. The residue was recrystallized from iso-propylether n-hexane to give a 2-chloro-5-hydroxy-α-(tert-butylaminomethyl)-benzylalcohol, m.p. 162° - 163° C. Hydrochloride: m.p. 245° - 248° C.

Workup

  1. temperatureunder cooling
  2. customThe reaction mixture was evaporated
  3. washwashed with ether
  4. extractionextracted with ether
  5. dry with materialThe extract was dried with Na2SO4
  6. customevaporated
  7. customThe residue was recrystallized from iso-propylether n-hexane

Sources & evidence

ORD record
ord-82fa38a5f7d9400c9863f9808d725c87
Source dataset
uspto-grants-1977_04
Patent number
US04018818

Reaction notes

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