1,2-Benzenedimethanol → N,N-Diisopropyl-1,5-dihydrobenzo[e][1,3,2]dioxaphosphepin-3-amine

HRID 258157

Reaction equation

HRID 258157 reaction equation
[OH:1][CH2:2][C:3]1[C:4](=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:5][OH:6].[CH:11]([N:14]([P:18](N(C(C)C)C(C)C)Cl)[CH:15]([CH3:17])[CH3:16])([CH3:13])[CH3:12]>C1COCC1>[CH:11]([N:14]([CH:15]([CH3:17])[CH3:16])[P:18]1[O:6][CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[CH2:2][O:1]1)([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 691531,2-Benzenedimethanol2×HCID 2733425Bis(diisopropylamino)chlorophosphine

Product 1

HCID 19782585N,N-Diisopropyl-1,5-dihydrobenzo[e][1,3,2]dioxaphosphepin-3-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Phthalyl alcohol (1.15 g, 8.31 mmol) was dissolved in 5 ml of THF, and bisdiisopropylaminochlorophosphine (2.21 g, 8.31 mmol) which was dissolved in 5 ml of THF was added dropwise to the solution at -15° C. under a nitrogen atmosphere. Afterward, the temperature of the solution was adjusted to room temperature, and after the disappearance of phthalyl alcohol had been confirmed, hydrochloride of diisopropylamine was washed with ether. The wash liquor was concentrated and then distilled in order to obtain the desired product having a melting point of from 150° to 155° C. (0.7 mmHg).

Workup

  1. additionwas added dropwise to the solution at -15° C. under a nitrogen atmosphere
  2. customwas adjusted to room temperature
  3. washhydrochloride of diisopropylamine was washed with ether
  4. concentrationThe wash liquor was concentrated
  5. distillationdistilled in order

Sources & evidence

ORD record
ord-9d568a1daaed4c6d917cab90fc95f644
Source dataset
uspto-grants-1993_11
Patent number
US05264605

Linked notes

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