Tetrahydrofuran → HCID 70256258, compound

HRID 378200Notes

Reaction equation

HRID 378200 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:24])([OH:23])[CH2:19][CH:18]=3)[CH2:13][CH2:12]2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:25]=[C:26]([CH3:28])[CH3:27].FC(F)(F)S(O)(=O)=O.[CH2:37](N(CC)CC)C.[CH2:44]1[CH2:48]OC[CH2:45]1>C(Cl)Cl.C(Cl)(Cl)Cl>[C:26]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:11]2[CH2:12][CH2:13][CH:14]([C:17]3[CH:18]=[CH:19][C:20]([CH3:24])([O:23][C:44]([CH3:45])([CH3:48])[CH3:37])[CH2:21][CH:22]=3)[CH2:15][CH2:16]2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1)([CH3:28])([CH3:27])[CH3:25]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 8255IsobutyleneHCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 70253044HCID 70253044, compound

Product 1

HCID 70256258HCID 70256258, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

In a mixture of 24 grams of THF and 43 grams of methylene chloride was dissolved 16.2 grams (0.05 mol) of 2-(4-hydroxyphenyl)-2-{4-(4-methyl-4-hydroxyphenyl)cyclohexyl}propane corresponding to formula (5f) wherein R4 is H. The solution was cooled to -30° C. with a dry ice/methanol bath. With stirring, 79.2 grams (1.4 mol) of liquid isobutene was added and 1.8 grams (0.012 mol) of trifluoromethanesulfonic acid was then added. Stirring was continued for 3 hours while keeping the reaction solution at a temperature of -10° C. to -5° C. Reaction was stopped by adding 2.4 grams (0.024 mol) of triethylamine to the reaction solution for neutralizing the acid. The reaction solution was mixed with 100 grams of chloroform and then washed three times with 100 grams of water. The solvent was distilled off from the organic layer, obtaining oily matter. The oil was purified by silica gel chromatography (eluent: chloroform/methanol), isolating 2-(4-tert-butoxyphenyl)2-{4-(4-methyl-4-tert-butoxyphenyl)cyclohexyl}propane corresponding to formula (5f) wherein R4 is a tert-butyl group. Amount 13.1 grams, yield 60.1%, purity 98.9%.

Workup

  1. stirringStirring
  2. customat a temperature of -10° C. to -5° C
  3. customReaction
  4. washwashed three times with 100 grams of water
  5. distillationThe solvent was distilled off from the organic layer
  6. customobtaining oily matter
  7. customThe oil was purified by silica gel chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-ff9267ea49494d3b82560209207bdb4c
Source dataset
uspto-grants-2000_02
Patent number
US06030746

Reaction notes

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