Hydroquinone → 2-Methoxy-4a,5,8,8a-tetrahydronaphthalene-1,4-dione

HRID 2260358Notes

Reaction equation

HRID 2260358 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:10])[CH:5]=[CH:6][C:7](=[O:9])[CH:8]=1.[C:11]1([CH:18]=CC(O)=[CH:14][CH:13]=1)O.CCOCC>C1(C)C=CC=CC=1.C=CC=C>[CH3:1][O:2][C:3]1[C:4](=[O:10])[CH:5]2[CH:6]([C:7](=[O:9])[CH:8]=1)[CH2:14][CH:13]=[CH:11][CH2:18]2

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 3283Diethyl EtherHCID 761462-Methoxy-1,4-benzoquinone

Product 1

HCID 108215692-Methoxy-4a,5,8,8a-tetrahydronaphthalene-1,4-dione

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 78451,3-ButadieneSolvent2×

Conditions

Temperature
60 °C

Procedure

A suspension of 2-methoxybenzoquinone (17, 750 mg, 5.43 mmol, TCI, used as received), hydroquinone (38 mg, Matheson, used as received) in toluene (7.5 mL) and butadiene (54, 7.5 mL, Matheson, used as received; Note: condensed butadiene into the toluene with ice bath cooling) contained in a screw top, sealed robe (Ace) was stirred overnight in a 60° C. oil bath. The resulting solution was allowed to cool to rt, then was further cooled in an ice bath. A precipitate formed. The sealed tube was opened. The solid was collected by filtration, washed with hexanes and allowed to air dry (930 mg). The solid was crystallized from hexanes (dissolved in 350 mL, hot filtered, concd to 200 mL, re-filtered, allowed to cool to rt) to yield a yellow powder (703 mg, 68%, >95% pure by 1H NMR analysis); mp 120°-122° C. (hexanes), lit. (Cavill et al., Aust. J. Chem. 26:595-601 (1993)) 126.5°-128° C. (ether); 1H NMR (CDCl3) δ2.21 (m, 2H), 2.51 (m, 2H), 3.16 (m, 1H), 3.26 (m, 1H), 3.79 (s, 3H), 5.69 (m, 2H), 5.90 (s, 1H).

Workup

  1. temperaturecooling)
  2. customsealed robe (Ace)
  3. temperatureto cool to rt
  4. temperaturewas further cooled in an ice bath
  5. customA precipitate formed
  6. filtrationThe solid was collected by filtration
  7. washwashed with hexanes
  8. customdry (930 mg)
  9. customThe solid was crystallized from hexanes (dissolved in 350 mL, hot filtered, concd to 200 mL, re-filtered, allowed to cool to rt)
  10. customto yield a yellow powder (703 mg, 68%, >95% pure by 1H NMR analysis)

Sources & evidence

ORD record
ord-a1d6d317bd534ddbb410bd9127cecdee
Source dataset
uspto-grants-1995_12
Patent number
US05476933

Reaction notes

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