Hydrochloric Acid → 2-Ethyl-4-tetradecylphenol

HRID 1639334Notes

Reaction equation

HRID 1639334 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)[CH3:23].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])[CH3:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 142562051-(2-Hydroxy-5-tetradecylphenyl)ethanone

Product 1

HCID 142562062-Ethyl-4-tetradecylphenolYield 72.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 23 g of 1-(2-hydroxy-5-tetradecylphenyl)ethanone, 5 g of 5% palladium on carbon catalyst, 10 ml of concentrated hydrochloric acid, 100 ml of water and 100 ml of glacial acetic acid was warmed to 50° C. and then hydrogenated in a Parr apparatus for 24 hours. This mixture was filtered, the solvent removed ad the residue dissolved in ether. The ether solution was washed with water, then a small amount of dilute aqueous sodium bicarbonate and dried. The residue was purified by HPLC, giving 16 g of the desired compound, mp 45.5°-46.5° C.

Workup

  1. filtrationThis mixture was filtered
  2. customthe solvent removed ad the residue
  3. dissolutiondissolved in ether
  4. washThe ether solution was washed with water
  5. dry with materiala small amount of dilute aqueous sodium bicarbonate and dried
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-69b61c0d2beb44309a27fb193d7265b2
Source dataset
uspto-grants-1989_11
Patent number
US04883816

Reaction notes

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