Triethylamine → HCID 19938496, compound

HRID 36380Notes

Reaction equation

HRID 36380 reaction equation
Cl[P:2]1[O:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][O:3]1.[C:10]([C:14]1[CH:19]=[C:18]([C:20](C)(C)C)[CH:17]=[C:16]([C:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=2)[C:15]=1[OH:30])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C1(C)C=C(C)C=C(C)C=1>[C:24]1([C:16]2[C:15]([O:30][P:2]3[O:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][O:3]3)=[C:14]([C:10]([CH3:12])([CH3:11])[CH3:13])[CH:19]=[C:18]([CH3:20])[CH:17]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 755081,3,2-Dioxaphosphorinane, 2-chloro-5,5-dimethyl-HCID 10541232HCID 10541232, compound2×

Product 1

HCID 19938496HCID 19938496, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Procedure

4.85 g (29.0 mmol) of 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane are added drop-wise over a period of about 15 minutes to a solution of 6.6 g (27.0 mmol) of 6-(cyclohexen-1-yl)-2-tert-butyl-4-methylphenol (compound (102), Example 1) and 4.0 ml (29.0 mmol) of triethylamine in 25 ml of mesitylene (1,3,5-trimethylbenzene). The reaction mixture is then refluxed for 18 hours, cooled, filtered, and the filtrate is concentrated on a vacuum rotary evaporator. Crystallization of the residue from dry acetonitrile gives 5.8 g (57%) of 2-[6-(cyclohexen-1-yl)-2-tert-butyl-4-methyl-phenoxy]-5,5-dimethyl-1,3,2-dioxaphosphorinane, m.p. 97°-102° C. (compound (201), Table 2).

Workup

  1. temperatureThe reaction mixture is then refluxed for 18 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated on a vacuum rotary evaporator
  5. customCrystallization of the residue from dry acetonitrile

Sources & evidence

ORD record
ord-3eb776d53dbb47d187b3886d19165e6e
Source dataset
uspto-grants-1995_05
Patent number
US05414033

Reaction notes

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