Formaldehyde → 3-tert-Butyl-2-hydroxybenzaldehyde

HRID 593376Notes

Reaction equation

HRID 593376 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 (6)(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. The crude 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 (CDCl3, 300 MHz): 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. extractionThe crude 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-b481d76a9ca1499e917573c87ef3b640
Source dataset
uspto-grants-2016_01
Patent number
US09242955B2

Reaction notes

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