Water → HCID 408360, compound

HRID 636949Notes

Reaction equation

HRID 636949 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[BH4-]>CC(O)C>[CH2:3]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 28123BorohydrideHCID 71643NorletimolHCID 4311764Sodium borohydride

Product 1

HCID 408360HCID 408360, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Sodium borohydride (0.2 g) was added in small portions to 3 mL of dry 2-propanol in a nitrogen atmosphere. To this mixture was added dropwise a solution of 1.0 g of 2-(benzylimino-methyl)-phenol in 3 mL of 2-propanol. After complete addition, stirring was continued for 1 h. Then water was added in order to decompose excess borohydride, and the volatiles were removed in vacuo. The residue was redissolved in ethyl acetate, washed with water, dried (sodium sulfate) and concentrated yielding 0.9 g of 2-(benzylamino-methyl)-phenol as an oil. EI-MS: 213 (M+).

Workup

  1. additionAfter complete addition
  2. customthe volatiles were removed in vacuo
  3. dissolutionThe residue was redissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e5c58b6a217b48718b255c5b288ea419
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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