Hydrochloric Acid → HCID 20374138, compound

HRID 1658037Notes

Reaction equation

HRID 1658037 reaction equation
[C:1]([C:5]1[C:10](O)=[C:9]([CH3:12])[C:8]([CH3:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:14].S(=O)(=O)(O)O.COC[O:23][CH3:24]>C1(C)C=CC=CC=1>[C:1]([C:5]1[C:24]([OH:23])=[C:7]([CH3:6])[C:8]([CH3:13])=[C:9]([CH:10]=1)[CH2:12][Cl:14])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 8020DimethoxymethaneHCID 170766Phenol, 6-(1,1-dimethylethyl)-2,3-dimethyl-

Product 1

HCID 20374138HCID 20374138, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30 grams of 6-tert.-butyl-2,3-dimethylphenol dissolved in 100 ml of toluene was added to 2.7 ml of concentrated hydrochloric acid containing 3.3 ml of concentrated sulfuric acid at 5° to 10°C. 26 grams of methylal was added dropwise to the above vigorously stirred dispersion over a period of about 15 minutes. After this the reaction mixture was heated at 36° to 37° for 2 hours while bubbling anhydrous gaseous hydrogen chloride through the reaction mixture. The reaction temperature was allowed to drop to 27° during the following 2 hours while continuing to bubble anhydrous hydrogen chloride through the reaction mixture. The acidic aqueous phase was separated from the reaction mixture after being extracted with toluene. The combined toluene phases were washed well with cold water and dried over anhydrous sodium sulfate. After filtering free of drying agent, the clear filtrate was freed of solvent by distillation at reduced pressures the resulting residue being crystallized from petroleum ether yielding the desired compound in the form of light yellow crystals melting at 92° to 95°C.

Workup

  1. temperatureAfter this the reaction mixture was heated at 36° to 37° for 2 hours
  2. customwhile bubbling anhydrous gaseous hydrogen chloride through the reaction mixture
  3. customto drop to 27° during the following 2 hours
  4. customto bubble anhydrous hydrogen chloride through the reaction mixture
  5. customThe acidic aqueous phase was separated from the reaction mixture
  6. extractionafter being extracted with toluene
  7. washThe combined toluene phases were washed well with cold water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtering free
  10. customof drying agent
  11. distillationthe clear filtrate was freed of solvent by distillation at reduced pressures the resulting residue
  12. custombeing crystallized from petroleum ether yielding the desired compound in the form of light yellow crystals melting at 92° to 95°C.

Sources & evidence

ORD record
ord-0bd1f5ae0e22481e8ca38cc8fbd4b675
Source dataset
uspto-grants-1976_06
Patent number
US03962377

Reaction notes

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