Hydroquinone → HCID 178459245, compound

HRID 1262485Notes

Reaction equation

HRID 1262485 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12](=[O:16])[CH2:13][CH2:14]Cl)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(C=CC(O)=CC=1)O.C(N(CC)CC)C>O1CCOCC1.C(Cl)(Cl)Cl>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12](=[O:16])[CH:13]=[CH2:14])[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 8471TriethylamineHCID 178444541HCID 178444541, compound

Product 1

HCID 178459245HCID 178459245, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

12.23 g of 1-(trans-4-pentylcyclohexyl)-3-chloropropan-1-one and 112 mg of hydroquinone were dissolved in 120 ml of absolute dioxan in a sulphonation flask with stirrer, thermometer, reflux condenser, dropping funnel and nitrogen gasification [in an analogous manner to Chem. Ber. 109 (1976) 3426 and 111 (1978) 2825] and 12.6 g of triethylamine were added dropwise within 10 minutes. The mixture was subsequently stirred at 80° C. for 3.5 hours, cooled to 15° C., the precipitated triethylamine hydrochloride was filtered off under suction, back-washed with 50 ml of dioxan and the solvent was evaporated on a rotary evaporator. The oil obtained was taken up in 100 ml of chloroform, washed firstly with 100 ml of 5% sodium hydrogen carbonate solution and then with 100 ml of water (the aqueous phases were each extracted with a small amount of chloroform), dried over sodium sulphate and freed from solvent. The oily 1-(trans-4-pentylcyclohexyl)-2-propen-1-one obtained was further processed without additional purification.

Workup

  1. temperaturethermometer, reflux condenser
  2. temperaturecooled to 15° C.
  3. filtrationthe precipitated triethylamine hydrochloride was filtered off under suction
  4. washback-washed with 50 ml of dioxan
  5. customthe solvent was evaporated on a rotary evaporator
  6. customThe oil obtained
  7. washwashed firstly with 100 ml of 5% sodium hydrogen carbonate solution
  8. extractioneach extracted with a small amount of chloroform),
  9. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-4a9b806539764a33b6cd5006b35ed5db
Source dataset
uspto-grants-1984_06
Patent number
US04452718

Reaction notes

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