Hydrochloric Acid → 5-(1,1-Dimethylethyl)-2-hydroxy-1,3-benzenedimethanol

HRID 746249

Reaction equation

HRID 746249 reaction equation
[OH-:1].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[C:14]1([OH:20])C=CC=CC=1.[CH2:21]=O.Cl>O.C(Cl)(Cl)Cl>[C:3]([C:7]1[CH:8]=[C:9]([CH2:21][OH:1])[C:10]([OH:13])=[C:11]([CH2:14][OH:20])[CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 996PhenolHCID 73934-tert-ButylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 1509815-(1,1-Dimethylethyl)-2-hydroxy-1,3-benzenedimethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37 percent) was added, and the solution was stirred for four to six days at ambient temperature. Concentrated hydrochloric acid (110 ml) was added, upon which a two-phase system forms. A yellow, oily organic phase was isolated and washed with three 500 ml portions of water. Chloroform (700 ml) and 500 ml of water were added to this organic oil and the mixture was stirred. The organic phase was isolated and dried over 100 g of anhydrous magnesium sulphate. Evaporation and cooling of the chloroform solution yielded a mixture of white crystals and oil. The addition of 50-100 ml of chloroform and filtration yielded a white crystalline product, 4-tert-butyl-2, 6-di(hydroxymethyl) phenol.

Workup

  1. dissolutiondissolved
  2. stirringthe solution was stirred for four to six days at ambient temperature
  3. customA yellow, oily organic phase was isolated
  4. washwashed with three 500 ml portions of water
  5. additionChloroform (700 ml) and 500 ml of water were added to this organic oil
  6. stirringthe mixture was stirred
  7. customThe organic phase was isolated
  8. dry with materialdried over 100 g of anhydrous magnesium sulphate
  9. customEvaporation
  10. temperaturecooling of the chloroform solution
  11. customyielded
  12. additiona mixture of white crystals and oil

Sources & evidence

ORD record
ord-5162f66797414001a8750acf3711ed38
Source dataset
uspto-grants-1986_07
Patent number
US04603185

Linked notes

Loading…