Diethyl Ether → HCID 20318401, compound

HRID 866819Notes

Reaction equation

HRID 866819 reaction equation
[C:1]([C:5]1[C:6]([OH:17])=[C:7]([CH3:16])[C:8]([CH3:15])=[C:9]([CH2:11][C:12]([OH:14])=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOCC>C1(C)C=CC=CC=1>[C:1]([C:5]1[C:6]([OH:17])=[C:7]([CH3:16])[C:8]([CH3:15])=[C:9]([CH2:11][C:12]([O:14][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8221Stearyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 20318410HCID 20318410, compound

Product 1

HCID 20318401HCID 20318401, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8.85 grams of 5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetic acid, 9.45 grams of n-octadecanol and 0.665 grams of p-toluenesulfonic acid monohydrate were dispersed in 500 ml of toluene and heated at reflux for seven hours. A little ether was added to the cooled reaction mixture to prevent precipitation. The reaction solution was then successively washed with water, saturated sodium bicarbonate solution and water once again until neutral. After drying over anhydrous sodium sulfate and filtering, the clear filtrate was concentrated at reduced pressures. After washing with cold acetonitrile, the dried ground residue was crystallized from n-heptane yielding white crystals melting at 79° to 81° (Compound 15).

Workup

  1. temperatureheated
  2. temperatureat reflux for seven hours
  3. customprecipitation
  4. washThe reaction solution was then successively washed with water, saturated sodium bicarbonate solution and water once again until neutral
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. filtrationfiltering
  7. concentrationthe clear filtrate was concentrated at reduced pressures
  8. washAfter washing with cold acetonitrile
  9. customthe dried ground residue was crystallized from n-heptane yielding white crystals melting at 79° to 81° (Compound 15)

Sources & evidence

ORD record
ord-f2f24a7bc3cb45de9c7dbb380c2c1cdf
Source dataset
uspto-grants-1978_07
Patent number
US04101550

Reaction notes

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