Phthalimide → Phosphonium, tetrabutyl-, hydroxide (1:1)

HRID 1724883Notes

Reaction equation

HRID 1724883 reaction equation
C([O-])(=O)C1C(=CC=CC=1)C(N)=[O:5].[CH2:13]([P+:17]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].C1(=O)NC(=O)C2=CC=CC=C12>>[OH-:5].[CH2:26]([P+:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:27][CH2:28][CH3:29]

Participants

3

Reactant 2

HCID 6809PhthalimideHCID 11983702HCID 11983702, compound

Product 1

HCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)Yield 40%

Procedure

Tetrabutylphosphonium phthalamate is also prepared in the following way. A solution of tetrabutylphosphonium hydroxide (12.5 g; 40% in water) is prepared. Then phthalimide (2.7 g) is added, and the reaction solution is stirred at room temperature overnight. The water is then removed in a rotary evaporator, and the residue is taken up in toluene. The toluene is removed in a rotary evaporator, and the residue is again taken up in toluene. This procedure is repeated 4-5 times. The solvent is then removed to dryness. 1H-NMR (d6-DMSO) 0.9 (t, 12 H), 1.42 (m, 16 H), 2.18 (m, 8 H), 7.05 (b, 1 H), 7.18 (m, 1 H), 7.29 (d, 2 H), 7.74 (d, 1 H), 10.35 (b, 1 H).

Workup

  1. customThe water is then removed in a rotary evaporator
  2. customThe toluene is removed in a rotary evaporator
  3. customThe solvent is then removed to dryness

Sources & evidence

ORD record
ord-b2001bba125f467da4b5ee3d8372dbce
Source dataset
uspto-grants-2009_02
Patent number
US07488818B2

Reaction notes

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