Tetrahydrofuran → alpha1-Phenyl-1,2-benzenedimethanol

HRID 260181Notes

Reaction equation

HRID 260181 reaction equation
[Li][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-:14].[Na+].[O-]S([O-])(=O)=O.[Mg+2].[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>C(Cl)Cl.O>[C:2]1([CH:6]([C:7]2[C:23]([CH2:24][OH:25])=[CH:22][CH:26]=[CH:3][CH:2]=2)[OH:14])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 178506676HCID 178506676, compound2×

Product 1

HCID 11424431alpha1-Phenyl-1,2-benzenedimethanolYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Phtalid was reacted with PhLi (1 eq, 2M in cyklohexane/diethylether 75/25) according to the general procedure. The reaction mixture was then transferred to a slurry of LiAlH4 in THF kept at 0° C. and under N2 -atmosphere. The temperature was raised to RT and the reaction mixture was stirred for 1.5 hour. H2O was added very slowly at 0° C., followed by NaOH (15%) and H2O. CH2Cl2 and MgSO4 was added. The mixture was filtrated with a glass filter funnel and the filtrate was evaporated to give 74% of 12B. 1H-NMR: 7.65-7.15 (m, 9H, Ar--H); 5.99 (s, 1H, CH(Ph)--OH); 4.63 (s, 1H, OH); 4.63 (s, 1H, OH); 4.59 (d, 1H, J=12 Hz, CH2 --OH); 4.42 (d, 1H, J=12 Hz, CH2 --OH);

Workup

  1. customkept at 0° C. and under N2
  2. filtrationThe mixture was filtrated with a glass
  3. filtrationfilter funnel
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b188ec234af4468283d9bbf681c65f5b
Source dataset
uspto-grants-1996_06
Patent number
US05525736

Reaction notes

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