Formaldehyde → 2-Hydroxy-5-tert-butylbenzyl alcohol

HRID 128342Notes

Reaction equation

HRID 128342 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:12].[Na+].[CH2:14]=O>O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:6]=1)[CH2:14][OH:12])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 73934-tert-ButylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 960202-Hydroxy-5-tert-butylbenzyl alcoholYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 1-liter Erlenmeyer flask 150 g (1.00 mole) of p-t-butylphenol, 56 g (1.4 formulas) of sodium hydroxide dissolved in 400 ml of water, and 120 ml (1.6 moles, 40 g CH2O/100 ml solution) of formaldehyde solution were combined. The mixture was kept at 50° in a water bath for 5 days with occasional swirling. (After 10 minutes the mixture had become a nearly clear solution, but cloudiness began to increase after an additional 5 minutes.) The precipitated solid product was suction filtered, washed with a little water, and sucked as dry as possible. This still moist salt was neutralized by treatment with about 600 ml of 10% acetic acid. The new solid which formed was filtered and washed with water to give 107.9 g, m.p. 65°-85°. Two recrystallizations from hexane with a small amount of ether added yielded 90.1 g (50%) of 5-t-butyl-2-hydroxybenzyl alcohol m.p. of 91°-92°. The NMR spectrum of this compound (3.1τ, multiplet, 3 protons, aromatic; 6.1, broad singlet, 2, OH; 5.42, singlet, 2,CH2 ; 8.80, singlet, 9, C(CH3)3) is interesting in that the two nonequivalent hydroxyls appear to give only one peak. This is probably caused by time averaging of the two hydroxy protons due to hydrogen bonding and the acidity of the phenolic proton.

Workup

  1. wait(After 10 minutes the mixture had become
  2. temperatureto increase after an additional 5 minutes
  3. washwashed with a little water
  4. customas dry as possible
  5. customThe new solid which formed
  6. filtrationwas filtered
  7. washwashed with water
  8. customto give 107.9 g, m.p. 65°-85°
  9. customTwo recrystallizations from hexane with a small amount of ether
  10. additionadded

Sources & evidence

ORD record
ord-b190aecfdd624489bf7d7e914f276738
Source dataset
uspto-grants-1981_03
Patent number
US04259464

Reaction notes

Loading…