Hydrochloric Acid → HCID 22595114, compound

HRID 1761292Notes

Reaction equation

HRID 1761292 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[C:13]([C:15]([CH3:22])([CH3:21])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=[CH:11][C:10]=1[OH:23])([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].N1C(C)=CC=CC=1C.Cl[Sn](Cl)(Cl)Cl.[CH2:37]=[O:38].Cl>C1(C)C=CC=CC=1>[CH3:8][C:2]([C:9]1[CH:14]=[C:13]([C:15]([CH3:22])([CH3:21])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=[C:11]([CH:37]=[O:38])[C:10]=1[OH:23])([CH3:1])[CH2:3][C:4]([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 79372,6-LutidineHCID 24287Tin tetrachlorideHCID 79870Phenol, 2,4-bis(1,1,3,3-tetramethylbutyl)-

Product 1

HCID 22595114HCID 22595114, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

2,4-bis(1,1,3,3-tetramethylbutyl)phenol (26.2 g, 82.4 mmol, synthesized by the method described in U.S. Pat. No. 3,373,210), toluene (200 ml) and 2,6-lutidine (14.4 g, 135 mmol) was placed in a stirred flask under a blanket of nitrogen and the mixture was cooled to 0° C. SnCl4 (8.57 g, 33 mmol) was then carefully added. The mixture was subsequently stirred at room temperature for 20 minutes, before paraformaldehyde (15.1 g, 502 mmol) was added. The mixture was then stirred at 100° C. for 12 hours. After cooling, hydrochloric acid (1 M, 272 ml) was added. The resulting suspension was filtered through Celite and the solid was washed with 100 ml of ethyl acetate. The organic phase of the filtrate was then separated off, washed twice with 100 ml of NaCl solution, dried over MgSO4 and evaporated at reduced pressure. A slightly yellowish oil was formed as product. According to GC/MS, this crude product contains only about 3% of starting material. Yield: 26.9 g (94%).

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. filtrationThe resulting suspension was filtered through Celite
  4. washthe solid was washed with 100 ml of ethyl acetate
  5. customThe organic phase of the filtrate was then separated off
  6. washwashed twice with 100 ml of NaCl solution
  7. dry with materialdried over MgSO4
  8. customevaporated at reduced pressure
  9. customA slightly yellowish oil was formed as product

Sources & evidence

ORD record
ord-30598c03e2d946e3916f757c48275b5a
Source dataset
uspto-grants-2005_01
Patent number
US06846961B2

Reaction notes

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