Hydrochloric Acid → 3-tert-Butyl-2-hydroxybenzaldehyde

HRID 1844683Notes

Reaction equation

HRID 1844683 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].CCN(CC)CC.[Mg+2].[Cl-].[Cl-].[CH2:22]=[O:23].Cl>C(#N)C>[C:1]([C:5]1[C:6]([OH:11])=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH:22]=[O:23])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 69232-Tert-ButylphenolHCID 8471TriethylamineHCID 5360315Magnesium Chloride

Product 1

HCID 36786753-tert-Butyl-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(tert-butyl)phenol (15 g, 0.1 mol), Et3N (37 g, 374 mmol), MgCl2 (14.3 g, 0.15 mol) and paraformaldehyde (20.2 g, 674 mmol) in ACN (200 mL) was heated at reflux for 5 h, cooled, poured into aq. HCl (2N, 200 mL) and extracted with Et2O. The organic layer was concentrated and purified by CC (PE/EA=8/1) to give compound P7a (13 g, 74%) as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. temperaturecooled
  4. extractionextracted with Et2O
  5. concentrationThe organic layer was concentrated
  6. custompurified by CC (PE/EA=8/1)
  7. customto give compound P7a (13 g, 74%) as a colorless oil

Sources & evidence

ORD record
ord-3297b81c9ebc43fd9a12cec07934f050
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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