Formaldehyde → 3-tert-Butyl-2-hydroxybenzaldehyde

HRID 2121280Notes

Reaction equation

HRID 2121280 reaction equation
[CH2:1]=[O:2].[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])([CH3:6])([CH3:5])[CH3:4].CC1C=CN=CC=1.[Sn](Cl)Cl>C1(C)C=CC=CC=1.C(OCC)C>[C:3]([C:7]1[C:8]([OH:13])=[C:9]([CH:10]=[CH:11][CH:12]=1)[CH:1]=[O:2])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 69232-Tert-ButylphenolHCID 79634-MethylpyridineHCID 24479Stannous Chloride

Product 1

HCID 36786753-tert-Butyl-2-hydroxybenzaldehydeYield 39.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
95 °C

Procedure

9.0 g (300 mmol) of para-formaldehyde in 200 ml of toluene were introduced into a 500 ml three-necked flask fitted with magnetic stirrer, reflux condenser and nitrogen/vacuum connection, and 15.4 ml (100 mmol) of 2-tert-butylphenol (Aldrich), 3.9 ml (40 mmol) of 4-methylpyridine and 1.89 g (10 mmol) of tin(II) chloride were added. The batch was subsequently allowed to stir at 95° C. for six hours. The isolated product was taken up in diethyl ether, and the solution was washed with sodium chloride solution, dried over sodium sulfate and evaporated in a rotary evaporator, giving the product in a yield of 39.5%.

Workup

  1. customfitted with magnetic stirrer
  2. temperaturereflux condenser
  3. washthe solution was washed with sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated in a rotary evaporator
  6. customgiving the product in a yield of 39.5%

Sources & evidence

ORD record
ord-352846b8ee1d4fa9aa415c575c4c7ad6
Source dataset
uspto-grants-2004_02
Patent number
US06695977B2

Reaction notes

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