Tributyl Phosphate → HCID 86609276, compound

HRID 1869615Notes

Reaction equation

HRID 1869615 reaction equation
[CH2:1]([P:5]([CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:6][CH:7]([CH3:9])[CH3:8])[CH:2]([CH3:4])[CH3:3].[CH2:14]([O:18][P:19]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])([O:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:20])[CH2:15][CH2:16][CH3:17]>>[CH2:22]([O:21][P:19]([O-:26])([O:18][CH2:14][CH2:15][CH2:16][CH3:17])=[O:20])[CH2:23][CH2:24][CH3:25].[CH2:10]([P+:5]([CH2:1][CH:2]([CH3:4])[CH3:3])([CH2:6][CH:7]([CH3:9])[CH3:8])[CH2:27][CH2:28][CH2:29][CH3:30])[CH:11]([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 31357Tributyl PhosphateHCID 107228Tris(2-methylpropyl)phosphine

Product 1

HCID 86609276HCID 86609276, compoundYield 68.5%

Procedure

Tri-iso-butylphosphine (206.5 g, 98%, 1.0 mole) was added dropwise over a period of 2 hours to a flask containing 271.8 g (98%, 1.0 mole) of tributylphosphate at 200° C. under nitrogen and stirring. When the addition was complete, the mixture was stirred at the same temperature for an additional 15 hours. The mixture was cooled down and moved to a rotary evaporator and dried under 160° C./5 mm Hg for 5 hours. The product (320.7 g, yield 68.5%) was pure judged from NMR and liquid at room temperature. 1H-NMR (CDCl3, 300.13 MHz, δ): 3.76 (q, 4H, 2×CH3CH2CH2—CH2O—), 2.19 (q, 6H, 3×CH3 (CH3)CH—CH2P+), 1.96 (m, 3H, 3×CH3 (CH3)CH—CH2P+), 1.96 (m, 2H, CH3CH2CH2—CH2P+), 1.44 (m, 8H, CH3—CH2CH2—CH2O—), 1.24 (m, 4H, CH3—CH2CH2—CH2P+), 1.01 (d, 18H, 3×CH3CH(CH3)—CH2P+), 0.84 (t, 3H, CH3—CH2CH2CH2P+), 0.77 (t, 6H, 2×CH3—CH2CH2CH2O—). 31P-NMR (CDCl3, 81.015 MHz, δ): 32.60 (P+), −0.61 [d, (RO)2—P(═O)—O−].

Workup

  1. additionWhen the addition
  2. stirringthe mixture was stirred at the same temperature for an additional 15 hours
  3. temperatureThe mixture was cooled down
  4. custommoved to a rotary evaporator
  5. customdried under 160° C./5 mm Hg for 5 hours

Sources & evidence

ORD record
ord-ab6d5de803db4d6182778eed2fd5dce8
Source dataset
uspto-grants-2009_12
Patent number
US07638636B2

Reaction notes

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