Methanol → 1,2-Bis(hydroxymethyl)-4,5-dimethylcyclohexa-1,4-diene

HRID 128767

Reaction equation

HRID 128767 reaction equation
CC(C[AlH]CC(C)C)C.[CH3:10][C:11]1[CH2:12][C:13]([C:22](OC)=[O:23])=[C:14]([C:18](OC)=[O:19])[CH2:15][C:16]=1[CH3:17].CO>ClCCl>[OH:19][CH2:18][C:14]1[CH2:15][C:16]([CH3:17])=[C:11]([CH3:10])[CH2:12][C:13]=1[CH2:22][OH:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 600973Dimethyl 4,5-dimethyl-1,4-cyclohexadiene-1,2-dicarboxylate

Product 1

HCID 152780381,2-Bis(hydroxymethyl)-4,5-dimethylcyclohexa-1,4-dieneYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of DIBAL in dichloromethane (1.0M, 45 ml, 0.045 mol) cooled to ice bath temperature under nitrogen was added dimethyl 4,5-dimethylcyclohexa-1,4-diene-1,2-dicarboxylate (2.24 g, 0.01 mol) in dry dichloromethane (30 ml) over 30 min. The resultant solution was stirred for a further 60 mins at this temperature after which methanol (10 ml) was added. The mixture was allowed to come to room temperature, filtered through a "Celite" pad, and the filtrate concentrated in vacuo to give an oil. Crystallisation from ethyl acetate/petroleum ether (40°-60° C.) gave the title compound in 35% yield. N.m.r: δH (90MHz, CD3OD) 4.15 (s,4H), 3.55 (bs,2H), 2.82 (s,4H), 1.69 ppm (s,6H)

Workup

  1. additionwas added
  2. customto come to room temperature
  3. filtrationfiltered through a "Celite" pad
  4. concentrationthe filtrate concentrated in vacuo
  5. customto give an oil
  6. customCrystallisation from ethyl acetate/petroleum ether (40°-60° C.)

Sources & evidence

ORD record
ord-518e2e1be6644aa4987e051789dc843a
Source dataset
uspto-grants-1995_11
Patent number
US05464873

Linked notes

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