Phosphonium, tetrabutyl-, hydroxide (1:1) → HCID 86626713, compound

HRID 1474583Notes

Reaction equation

HRID 1474583 reaction equation
[C:1]([NH:4][CH2:5][C:6]([O-:8])=[O:7])(=[O:3])[CH3:2].[OH-].[CH2:10]([P+:14]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH3:13]>>[C:1]([NH:4][CH2:5][C:6]([O-:8])=[O:7])(=[O:3])[CH3:2].[CH2:23]([P+:14]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:24][CH2:25][CH3:26]

Participants

3

Reactant 2

HCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)HCID 1550976HCID 1550976, compound

Product 1

HCID 86626713HCID 86626713, compoundYield 102.2%

Procedure

At 0° C., 3.54 g of N-acetylglycinate (by Tokyo Chemical) was added to 20.0 g of tetrabutylphosphonium hydroxide (aqueous 41.4% solution, by Hokko Chemical), and stirred for 10 minutes. Using an evaporator, the pressure was reduced to 40 to 50 mmHg, and this was concentrated at 60 to 80° C. for 2 hours, and then at 90° C. for 5 hours. At room temperature, this was again dissolved in 14.2 ml of ethyl acetate (Junsei Chemical). Using an evaporator, the pressure was reduced to 40 to 50 mmHg, and this was concentrated at 70 to 90° C. for 3 hours. Thus, 11.7 g of tetrabutylphosphonium N-acetylglycinate (purity: 96.9%) was obtained as an oily compound. The obtained ionic liquid had the same properties as in Production Example 16.

Workup

  1. customan evaporator
  2. concentrationthis was concentrated at 60 to 80° C. for 2 hours
  3. waitat 90° C. for 5 hours
  4. dissolutionAt room temperature, this was again dissolved in 14.2 ml of ethyl acetate (Junsei Chemical)
  5. customan evaporator
  6. concentrationthis was concentrated at 70 to 90° C. for 3 hours

Sources & evidence

ORD record
ord-5b61465a4f7b46ccba48fdc59f0d3bd0
Source dataset
uspto-grants-2015_04
Patent number
US09018321B2

Reaction notes

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