Diethyl Ether → HCID 20040591, compound

HRID 1763103Notes

Reaction equation

HRID 1763103 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])C=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13]([O:15][C:16]([C:18]([P:25]([O:30][CH2:31][CH3:32])(=[O:29])[O:26][CH2:27][CH3:28])([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[CH3:19])=[O:17])[CH3:14].[CH3:33]COCC>>[C:1]([C:5]1[C:6]([OH:7])=[CH:8][C:23]([C:22]([CH3:33])([CH3:24])[CH2:21][CH2:20][C:18]([C:16]([O:15][CH2:13][CH3:14])=[O:17])([P:25]([O:26][CH2:27][CH3:28])(=[O:29])[O:30][CH2:31][CH3:32])[CH3:19])=[C:10]([OH:12])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 16043Tert-ButylhydroquinoneHCID 19864985Ethyl 2-(diethoxyphosphoryl)-2,5-dimethylhex-4-enoate

Product 1

HCID 20040591HCID 20040591, compound

Procedure

41.4 Parts of 2-t-butylhydroquinone, 15.3 parts of diethyl 2-ethoxycarbonyl-5-methyl-hex-4-ene-2-phosphonate, and 5.0 parts of Fulmont® 237 are stirred at 130° C. for 24 hours. The cooled reaction is diluted with ether, washed with 10% sodium hydroxide solution and then with water. After stripping off the ether, the residual oil is distilled and gives a fraction b0.4 89°-156° C. and a residue. This residue is chromatographed on a column established from 150 parts silica, and an initial solvent mixture comprising petroleum-ether (b.p. 40°-60° C.) and 5% ethylacetate. Column elution is carried out by increasing the percentage of ether, and ultimately with 50% ether present, diethyl 5-(4'-t-butyl-2',5'-dihydroxyphenyl)-2-ethoxycarbonyl-5-methyl-hexane-2-phosphonate is obtained as a viscous oil with the following percentage composition by weight.

Workup

  1. customThe cooled reaction
  2. washwashed with 10% sodium hydroxide solution
  3. distillationthe residual oil is distilled
  4. customgives a fraction b0.4 89°-156° C.
  5. customThis residue is chromatographed on a column
  6. washColumn elution
  7. temperatureby increasing the percentage of ether

Sources & evidence

ORD record
ord-66be374fae5546f88a0a7bac9efbf4b1
Source dataset
uspto-grants-1989_05
Patent number
US04835323

Reaction notes

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