Water → HCID 408360, compound

HRID 2304275Notes

Reaction equation

HRID 2304275 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-2b9f64a80c3442f5b3906e43c9ea30bc
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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