Phthalic Anhydride → cis-1,2-Dihydroxymethylcyclohex-4-ene

HRID 1376477Notes

Reaction equation

HRID 1376477 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1(=O)[O:12][C:10](=[O:11])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12>C1COCC1>[OH:11][CH2:10][C@@H:9]1[CH2:13][CH:14]=[CH:15][CH2:16][C@@H:8]1[CH2:7][OH:12]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 21226445Aluminium lithium hydride

Product 1

HCID 11275057cis-1,2-Dihydroxymethylcyclohex-4-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. suspension of lithium aluminum hydride (4 eq) in dry THF (250 mL) was added portionwise phtalic anhydride over 20 minutes. The mixture was brought to room temperature then warmed to reflux for 6 hours then cooled to 0° C. The reaction was quenched with saturated sodium sulfate solution, filtered and concentrated. The residue was taken into ethyl acetate washed with water, brine, dried and concentrated to yield the desired compound as a viscous oil. 1HNMR (500 mHz, CDCl3): 5.62 ppm (s, 2H); 3.76-3.70 (m, 2H); 3.72-3.55 (m, 4H), 2.20-1.98 (m, 6H).

Workup

  1. customwas brought to room temperature
  2. temperaturethen warmed
  3. temperatureto reflux for 6 hours
  4. customThe reaction was quenched with saturated sodium sulfate solution
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washwashed with water, brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c12f0a89a7db4c939ad065594a5d1394
Source dataset
uspto-grants-1997_09
Patent number
US05663175

Reaction notes

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