Hydrochloric Acid → 2-Hexyl-4-tetradecylphenol

HRID 329983Notes

Reaction equation

HRID 329983 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:4][C:3]=1[C:22](=O)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].Cl.O>[Pd].C(O)(=O)C>[CH2:22]([C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:6]=[CH:7][C:2]=1[OH:1])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 142562081-(2-Hydroxy-5-tetradecylphenyl)-1-hexanone

Product 1

HCID 150302662-Hexyl-4-tetradecylphenolYield 41.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 31.04 g of 1-(2-hydroxy-5-tetradecylphenyl)-1-hexanone, 8.4 g of 5% palladium on carbon, 5 ml of concentrated hydrochloric acid, 95 ml of water and 100 ml of glacial acetic acid was hydrogenated in a Parr apparatus for 16 hours, then filtered and the solvents removed. The residue was chromatographed on silica gel, eluting with hexane:ethyl acetate (40:1), giving 12.3 g of the desired compound.

Workup

  1. filtrationfiltered
  2. customthe solvents removed
  3. customThe residue was chromatographed on silica gel
  4. washeluting with hexane:ethyl acetate (40:1)

Sources & evidence

ORD record
ord-fbe0e4e0f905433994e4448a9453a23e
Source dataset
uspto-grants-1990_01
Patent number
US04894367

Reaction notes

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