Benzyl Chloride → {(1R,6S)-6-[(Benzyloxy)methyl]cyclohex-3-en-1-yl}methanol

HRID 1086334Notes

Reaction equation

HRID 1086334 reaction equation
[OH:1][CH2:2][C@H:3]1[C@@H:8]([CH2:9][OH:10])[CH2:7][CH:6]=[CH:5][CH2:4]1.[H-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[OH:1][CH2:2][C@H:3]1[C@@H:8]([CH2:9][O:10][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][CH:6]=[CH:5][CH2:4]1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 11275057cis-1,2-Dihydroxymethylcyclohex-4-ene

Product 1

HCID 67946542{(1R,6S)-6-[(Benzyloxy)methyl]cyclohex-3-en-1-yl}methanolYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The diol (1) (16.2 g) in dimethylformamide (50 ml) is added dropwise to sodium hydride (3.1 g) in dimethylformamide (DMF) (50 ml). The mixture is stirred for 20 minutes and then benzyl chloride (16 g) is added and stirring is continued for a further 18 hours at 70° C. After removing the DMF in vacuo, water is added and the mixture is extracted with ether. The combined extracts are dried (MgSO4) and the solvent is evaporated to give a residue which is distilled under reduced pressure to give the title compound as an oil (16.5 g, ca. 60%), b.p. 140°-145° C./0.03 mm, νmax (film) 3440 and 1600 cm-1.

Workup

  1. stirringstirring
  2. waitis continued for a further 18 hours at 70° C
  3. customAfter removing the DMF in vacuo, water
  4. additionis added
  5. extractionthe mixture is extracted with ether
  6. dry with materialThe combined extracts are dried (MgSO4)
  7. customthe solvent is evaporated
  8. customto give a residue which
  9. distillationis distilled under reduced pressure

Sources & evidence

ORD record
ord-2bea88dc9c3a47d9a3c8612b7eca4ecd
Source dataset
uspto-grants-1991_07
Patent number
US05028733

Reaction notes

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