Sodium Hydroxide → HCID 54402218, compound

HRID 542712Notes

Reaction equation

HRID 542712 reaction equation
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[CH3:9][C:10]1([CH3:33])[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]2[CH:15]=[C:14]([C:22]([CH3:32])=[CH:23][C:24]3[CH:31]=[CH:30][C:27]([CH2:28][OH:29])=[CH:26][CH:25]=3)[CH:13]=[CH:12][C:11]1=2.[OH-].[Na+]>C(Cl)(Cl)(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[P:1]([O:5][CH2:6][CH3:7])([O:2][CH2:3][CH3:4])([O:29][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([CH:23]=[C:22]([C:14]2[CH:13]=[CH:12][C:11]3[C:10]([CH3:33])([CH3:9])[CH2:19][CH2:18][C:17]([CH3:20])([CH3:21])[C:16]=3[CH:15]=2)[CH3:32])=[CH:25][CH:26]=1)=[O:8]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 126321HCID 126321, compoundHCID 3780918Diethylphosphite

Product 1

HCID 54402218HCID 54402218, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 3.5 g (25 mmol) of diethyl phosphite in 6 ml of carbon tetrachloride was added dropwise, while cooling with ice, to a mixture of 7 g (20 mmol) of 4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propenyl]-benzyl alcohol, 12 ml of carbon tetrachloride, 0.16 g of tetrabutylammonium bromide and 6 ml of 50% strength sodium hydroxide solution. The mixture was stirred for 3 days at room temperature, then extracted with 30 ml of methylene chloride, the organic phase was washed with 10 ml of 2% strength hydrochloric acid and twice with 10 ml of water each time, and was dried over Na2SO4 and evaporated down. The residue was recrystallized from pentane and once again from petroleum ether, to give 0.3.g of the title compound of melting point 70°-74° C., which was 98% pure according to HPLC (C18 reverse phase; hexane/ethanol/0.1% strength acetic acid; 100 ml/min.).

Workup

  1. extractionextracted with 30 ml of methylene chloride
  2. washthe organic phase was washed with 10 ml of 2% strength hydrochloric acid and twice with 10 ml of water each time
  3. dry with materialwas dried over Na2SO4
  4. customevaporated down
  5. customThe residue was recrystallized from pentane and once again from petroleum ether

Sources & evidence

ORD record
ord-396ab21d90d34882a58e0f2773d4c71d
Source dataset
uspto-grants-1987_04
Patent number
US04659701

Reaction notes

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