Bisphenol A → HCID 13343962, compound

HRID 1461977Notes

Reaction equation

HRID 1461977 reaction equation
[C:1]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N([CH2:23][CH3:24])CC)C.[P:25](=[O:34])(Cl)([S:29][CH2:30][CH2:31][CH3:32])[O:26][CH2:27][CH3:28]>C(#N)C>[CH2:27]([O:26][P:25]([O:17][C:14]1[CH:13]=[CH:12][C:11]([C:1]([C:4]2[CH:5]=[CH:6][C:7]([O:10][P:25]([S:29][CH2:30][CH2:23][CH3:24])([O:26][CH2:27][CH3:28])=[O:34])=[CH:8][CH:9]=2)([CH3:3])[CH3:2])=[CH:16][CH:15]=1)([S:29][CH2:30][CH2:31][CH3:32])=[O:34])[CH3:28]

Participants

5

Reactant 3

HCID 6623Bisphenol AHCID 8471TriethylamineHCID 11745722O-Ethyl S-propyl chlorothiophosphate

Product 1

HCID 13343962HCID 13343962, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
10 °C

Procedure

To a 250 ml round bottom flask equipped with a water condenser, drying tube, magnetic stirrer, and addition funnel was added 4,4'-isopropylidenediphenol (4.57 g, 20 mmol), triethylamine (4.24 g, 42 mmol), and acetonitrile (75 ml). The solution was cooled to 10° C. and O-ethyl S-n-propyl phosphorochloridothioate (8.30 g, 41 mmol) in acetonitrile (25 ml) was added dropwise over 15 minutes. The cooling bath was removed and the reaction warmed to 35° C. for 4 hours. The reaction was diluted with ether (500 ml) and washed successively with water (2×50 ml), 1M NaOH (2×50 ml), 1% HCl (2×50 ml), and brine (2×50 ml). The organic solution was dried (MgSO4) and concentrated under reduced pressure to give the desired product as a colorless oil (6.50 g, 10.8 mmol).

Workup

  1. customTo a 250 ml round bottom flask equipped with a water condenser
  2. customdrying
  3. additiontube, magnetic stirrer, and addition funnel
  4. customThe cooling bath was removed
  5. temperaturethe reaction warmed to 35° C. for 4 hours
  6. additionThe reaction was diluted with ether (500 ml)
  7. washwashed successively with water (2×50 ml), 1M NaOH (2×50 ml), 1% HCl (2×50 ml), and brine (2×50 ml)
  8. dry with materialThe organic solution was dried (MgSO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-befe36765603456192494617e8de10b1
Source dataset
uspto-grants-1984_07
Patent number
US04457922

Reaction notes

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