Hydrochloric Acid → HCID 20361461, compound

HRID 1679782Notes

Reaction equation

HRID 1679782 reaction equation
[C:1]([C:5]1[C:10](O)=[C:9]([CH3:12])[C:8]([CH3:13])=C[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:14].S(=O)(=O)(O)O.COC[O:23][CH3:24].[C:25]1(C)C=CC=CC=1>>[C:1]([C:5]1[C:10]([CH2:25][Cl:14])=[C:9]([CH3:12])[C:8]([CH3:13])=[C:24]([OH:23])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 1140TolueneHCID 8020DimethoxymethaneHCID 170766Phenol, 6-(1,1-dimethylethyl)-2,3-dimethyl-

Product 1

HCID 20361461HCID 20361461, compound

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 which the reaction mixture was heated at 36° to 37° for 2 hours while bubbling anhydrous gaseous 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 thorugh the reaction mixture. The acidic aqueous phase was separated from the reaction mixture after being extracted with toluene and the combined toluene phases 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. temperaturewas heated at 36° to 37° for 2 hours
  2. customwhile bubbling anhydrous gaseous chloride through the reaction mixture
  3. customto drop to 27° during the following 2 hours
  4. customto bubble anhydrous hydrogen chloride thorugh 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 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-c32cf8cc5cb445c3aa1b299ac6a1faee
Source dataset
uspto-grants-1978_03
Patent number
US04081475

Reaction notes

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