HCID 54211985, compound → HCID 13187532, compound

HRID 462466Notes

Reaction equation

HRID 462466 reaction equation
[CH:1]1([O:7][CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17]CC3C=CC=CC=3)=[CH:13][CH:12]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([O:7][CH2:8][CH2:9][C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 54211985HCID 54211985, compound

Product 1

HCID 13187532HCID 13187532, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 23938PalladiumCatalyst

Procedure

16 g (0.049 mol) of cyclohexyloxymethyl (4-benzyloxyphenyl) methanone are hydrogenated under a hydrogen pressure of 50 psi, at a temperature of 35 to 40° C., in solution in 150 cc of methanol containing a few drops of 70% HClO4 solution and 1 g of 5% palladium-on-charcoal. The catalyst is filtered off, the solvent is evaporated off in vacuo and the residual oil is chromatographed on a silica column (eluent: 8/2 cyclohexane/ethyl acetate). An oil is collected which has a refractive index nD18 =1.5335; boiling point 0.01=130° C.

Workup

  1. customat a temperature of 35 to 40° C.
  2. filtrationThe catalyst is filtered off
  3. customthe solvent is evaporated off in vacuo
  4. customthe residual oil is chromatographed on a silica column (eluent: 8/2 cyclohexane/ethyl acetate)
  5. customAn oil is collected which
  6. custompoint 0.01=130° C.

Sources & evidence

ORD record
ord-35c2f52b19dd46d2a607287cfabbe188
Source dataset
uspto-grants-1985_05
Patent number
US04515814

Reaction notes

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