Diethyl Ether → HCID 20318401, compound

HRID 1287344Notes

Reaction equation

HRID 1287344 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 7 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 anyhyrous 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 cyrstals melting at 79° to 81° (Compound 15).

Workup

  1. temperatureheated
  2. temperatureat reflux for 7 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 anyhyrous 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 cyrstals melting at 79° to 81° (Compound 15)

Sources & evidence

ORD record
ord-5a69a892ead54915b7e75691a22863e2
Source dataset
uspto-grants-1976_10
Patent number
US03984460

Reaction notes

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