Hydrochloric Acid → HCID 22040026, compound

HRID 1790546Notes

Reaction equation

HRID 1790546 reaction equation
[CH2:1]1N2CN3CN(C2)CN1C3.C[C:12]1[CH:17]=[C:16]([CH2:18][CH2:19][CH3:20])[CH:15]=C[C:13]=1[OH:21].Cl.F[C:24](F)(F)[C:25]([OH:27])=O>C(OCC)(=O)C>[OH:27][C:25]1[C:24]([CH3:1])=[CH:15][C:16]([CH2:18][CH2:19][CH3:20])=[CH:17][C:12]=1[CH:13]=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 876434-Propyl-o-cresol

Product 1

HCID 22040026HCID 22040026, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4.2 g of hexamethylenetetramine were cautiously added to 1.5 g of 2-methyl-4-propyl-phenol in 11 ml of trifluoroacetic acid and the mixture was heated for 5 hrs. to 120° C. After the addition of 11 ml of 1N hydrochloric acid the mixture was stirred for 1 hr. at 107° C. The mixture was cooled to room temperature, diluted with ethyl acetate and washed in sequence with water, dilute sodium hydrogen carbonate solution, water and sodium chloride solution. Evaporation of the solution and chromatography on silica gel with hexane-toluene gave 2-hydroxy-3-methyl-5-propyl-benzaldehyde. MS: 178 (M)+.

Workup

  1. temperaturethe mixture was heated for 5 hrs
  2. customto 120° C
  3. customat 107° C
  4. washwashed in sequence with water, dilute sodium hydrogen carbonate solution, water and sodium chloride solution
  5. customEvaporation of the solution and chromatography on silica gel with hexane-toluene

Sources & evidence

ORD record
ord-066c90e585734d8794466e96dcddc3e2
Source dataset
uspto-grants-2006_07
Patent number
US07071212B2

Reaction notes

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