Formaldehyde → 3-tert-Butyl-2-hydroxybenzaldehyde

HRID 919199Notes

Reaction equation

HRID 919199 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Mg+2].[Cl-].[CH2:15]=[O:16].C(N(CC)CC)C>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:15]=[O:16])[C:6]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 69232-Tert-ButylphenolHCID 8471TriethylamineHCID 5360315Magnesium Chloride

Product 1

HCID 36786753-tert-Butyl-2-hydroxybenzaldehydeYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 2-tert-butylphenol (3)(4.55 g, 30 mmol), magnesium chloride (5.71 g, 60 mmol) and paraformaldehyde (2.08 g, 66 mmol) in THF (120 mL) at room temperature, was added triethylamine (8.35 mL, 60 mmol) dropwise. The reaction was heated to reflux for 3 hours to give an orange suspension. This was extracted using EtOAc (3×50 mL). A small amount of diluted HCl can be added if a permanent emulsion is formed. The organic layers were dried over MgSO4 and the volatiles evaporated under low pressure to yield a pale yellow oil which did not need any further purification. It can become dark green on storage. Yield: 90%. Pale yellow oil. 1H-NMR δH: 1.44 (9H, s, 3×CH3), 6.97 (1H, t, J=7.5 Hz, HAr), 7.41 (1H, dd, J=1.5 Hz, J=7.5 Hz, HAr), 7.54 (1H, dd, J=1.2 Hz, J=7.5 Hz, HAr), 9.88 (1H, s, CHO), 11.82 (1H, s, OH).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hours
  3. customto give an orange suspension
  4. extractionThis was extracted
  5. additionA small amount of diluted HCl can be added if a permanent emulsion
  6. customis formed
  7. dry with materialThe organic layers were dried over MgSO4
  8. customthe volatiles evaporated under low pressure
  9. customto yield a pale yellow oil which
  10. customany further purification

Sources & evidence

ORD record
ord-c7e3a05124f948ba91985800d7d4efa9
Source dataset
uspto-grants-2016_03
Patent number
US09273024B2

Reaction notes

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