Hydrochloric Acid → HCID 178450140, compound

HRID 1906350Notes

Reaction equation

HRID 1906350 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[OH:5][C:6]1[CH2:11][CH:10]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[CH2:9][C:8](=[O:21])[C:7]=1[C:22](=[O:25])[CH2:23][CH3:24].[C:26](Cl)(=[O:30])/[CH:27]=[CH:28]/[CH3:29].Cl>ClCCl>[OH:21][C:8]1[CH2:9][CH:10]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[C:14]([C:26](=[O:30])/[CH:27]=[CH:28]/[CH3:29])[C:13]=2[CH3:20])[CH2:11][C:6](=[O:5])[C:7]=1[C:22](=[O:25])[CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 643131trans-Crotonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178458835HCID 178458835, compound

Product 1

HCID 178450140HCID 178450140, compoundYield 115.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of aluminum trichloride (4.0 g, 0.03 mole) in dichloromethane (20 ml) at 0° C. was added 3-hydroxy-5-mesityl-2-propionylcyclohex-2-en-1-one (2.9, 0.01 mole) in dichloromethane (10 ml). The mixture was stirred at 0° C. for five minutes and then crotonyl chloride (1.1 g, 0.01 mole) was added. Stirring was continued at 0° C. for 30 minutes and then at 20° C. for 3 hours. The brown solution was poured into cold dilute hydrochloric acid (2M, 200 ml) and shaken occasionally as it was allowed to warm to room temperature. The organic phase was separated and the aqueous phase was shaken with chloroform (2×100 ml). The combined organic extracts were dried over magnesium sulphate and evaporated to give 3-hydroxy-5-(3-crotonyl-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one (4.1 g, 83%) as a pale brown oil. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.16 (3H, t); 1.93 (3H, d, J=7 Hz); 2.07 (3H, s); 2.17 (3H, s); 2.38 (3H, s); 2.2-4.0 (7H, m); 6.1-6.8 (2H, m); 6.86 (1H, s); 18.20 (1H, s).

Workup

  1. stirringStirring
  2. waitwas continued at 0° C. for 30 minutes
  3. waitat 20° C. for 3 hours
  4. stirringshaken occasionally as it
  5. temperatureto warm to room temperature
  6. customThe organic phase was separated
  7. stirringthe aqueous phase was shaken with chloroform (2×100 ml)
  8. dry with materialThe combined organic extracts were dried over magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-6a8917a427034c9b8cd43d83fd5c485b
Source dataset
uspto-grants-1987_03
Patent number
US04652303

Reaction notes

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