HCID 12906145, compound → HCID 12906147, compound

HRID 1390575Notes

Reaction equation

HRID 1390575 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[CH:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].[H][H]>C(O)(=O)C.[Pd]>[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17]

Participants

5

Reactant 2

HCID 12906145HCID 12906145, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 12906147HCID 12906147, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1-(2'-hydroxy-3',4',6'-trimethylphenyl)-1,6-hexanediol (formula III-3 wherein R=H3C, X=H, Y=OH, n=4, in the free form) (5.43 parts) in acetic acid (150 volume parts) was stirred with 5% palladium on carbon (4.79 parts) under a stream of hydrogen gas at room temperature until the uptake of hydrogen ceased. The catalyst was filtered off and the filtrate was concentrated in vacuo. The resulting residue was subjected to column chromatography on silica gel and eluted with chloroform-methanol (100:1). From the 1st fraction, 6-(2'-hydroxy-3',4',6'-trimethylphenyl)hexanol (formula III-2, wherein R=H3C, X=H, Y=OH, n=4, in the free form) (0.872 part) was obtained as colorless needles melting at 81°-82° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. washeluted with chloroform-methanol (100:1)

Sources & evidence

ORD record
ord-a76e149b843d42be82b57bfbc7b01036
Source dataset
uspto-grants-1979_02
Patent number
US04139545

Reaction notes

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