Ammonium Chloride → 4-(Hydroxymethyl)-2-methylphenol

HRID 1269596

Reaction equation

HRID 1269596 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].[B-].CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].[NH4+]>C(Cl)Cl>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([CH3:10])[CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 1399014-Hydroxy-3-methylbenzaldehydeHCID 9881569Tetra-N-butylammonium borohydride

Product 1

HCID 142518564-(Hydroxymethyl)-2-methylphenolYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-3-methylbenzaldehyde (10 g, 73.5 mmol) in dry CH2Cl2 (550 mL) under nitrogen at 5° C. was added tetra-N-butylammonium borohydride (20.58 g, 80 mmol) and the resultant mixture stirred for 1.25 h at 5° C. Saturated ammonium chloride solution (30 mL) was added to the reaction mixture and the resultant mixture stirred for 1 h at 5° C. Saturated ammonium chloride solution (60 mL) was added and the reaction mixture extracted with CH2Cl2, dried (Na2SO4) and the solvents removed in vacuo. Purification by flushing through silica (2×150 g) eluting with EtOAc afforded the title compound as an oily yellow solid (8.01 g).

Workup

  1. extractionthe reaction mixture extracted with CH2Cl2
  2. dry with materialdried (Na2SO4)
  3. customthe solvents removed in vacuo
  4. customPurification
  5. customby flushing through silica (2×150 g)
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-65f961eafc8b4085a7dad5f5dd583874
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Linked notes

Loading…