2,3,4-Trimethoxybenzaldehyde → (2,3,4-Trimethoxyphenyl)methanol

HRID 2351819Notes

Reaction equation

HRID 2351819 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[BH4-].[Na+].C1CCCCC1.CCOC(C)=O>C(Cl)Cl.C(O)C>[OH:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([O:13][CH3:14])=[C:10]([O:11][CH3:12])[C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 750062,3,4-TrimethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 123571(2,3,4-Trimethoxyphenyl)methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

2 g of commercials 2,3,4-trimethoxybenzaldehyde are placed in a 100 ml three-necked flask equipped with a magnetic stirrer, a gas inlet and a thermometer and are dissolved in 15 ml of CH2Cl2 +5 ml of ethanol. 200 mg of NaBH4 (6 mmoles) are added in small portions, at ambient temperature. The contents are stirred for 30 minutes at ambient temperature. TLC (cyclohexane:AcOEt 6:4) indicates a single-spot product. The ethanol is evaporated off and the residue is taken up with ChCl3, the organic phases are washed with NaCl and then with H2O, dried over MgSO4 and evaporated. An analytically pure pale yellow oil is obtained (Y=98%).

Workup

  1. customequipped with a magnetic stirrer, a gas inlet
  2. customThe ethanol is evaporated off
  3. washthe organic phases are washed with NaCl
  4. dry with materialwith H2O, dried over MgSO4
  5. customevaporated
  6. customAn analytically pure pale yellow oil is obtained (Y=98%)

Sources & evidence

ORD record
ord-d05e0023c8994e0f90127cd855485c48
Source dataset
uspto-grants-1989_10
Patent number
US04873349

Reaction notes

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