Hydrochloric Acid → 2,4-tert-butyl-6-hydroxym ethyl-phenol

HRID 1904054Notes

Reaction equation

HRID 1904054 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH2:16]=[O:17].B(O)(O)O.Cl>CCOCC.CCCCC.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH2:16][OH:17])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 73112,4-Di-tert-butylphenolHCID 7628Boric Acid

Product 1

HCID 5262032,4-tert-butyl-6-hydroxym ethyl-phenol

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Conditions

Temperature
80 °C

Procedure

2,4-Di-t-butylphenol (20.63 gr., 0.1 mole), paraformaldehyde (3.0 gr., 0.1 mol), boric acid (6.18 g., 0.1 mol) and toluene (50 ml.) were charged into a flask and heated at 80° C. under nitrogen for 48 hours. The mixture was filtered and the solvent removed to provide a brown oil. This oil was dissolved in ether and stirred with an equal volume of 1 N HCl for 2 hours. The ether layer was removed, washed with water, dried (MgSO4) and evaporated to form a soft yellow solid. This solid was stirred in pentane and then filtered to afford a white solid with a melting point of 97°-99° C. The structure was confirmed by NMR and FD/MS.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent removed
  3. customto provide a brown oil
  4. customThe ether layer was removed
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto form a soft yellow solid
  9. filtrationfiltered
  10. customto afford a white solid with a melting point of 97°-99° C

Sources & evidence

ORD record
ord-d3c16c24d6894ae9be01a77253f270db
Source dataset
uspto-grants-1984_03
Patent number
US04439564

Reaction notes

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