Acetone → (2-Carboxyethyl)triphenylphosphonium chloride

HRID 128662

Reaction equation

[Cl:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[C:7]1([P:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCOCC.CC(C)=O>C(Cl)(Cl)Cl>[Cl-:1].[C:4]([CH2:3][CH2:2][P+:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)([OH:6])=[O:5]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 5.4 g (50 mmol) of 3-chloropropionic acid and 13.1 g (50 mmol) of triphenylphosphine were heated for 2 hours at 145° C. and 2 hours at 95° C. The product, a glassy solid, was dissolved in 200 mL of CHCl3, to which was added 100 mL of Et2O. The volume was reduced to 250 mL. 5 mL of acetone was added to the solution. After 2 hours, 10.98 g of a solid was collected and used immediately in the manner described in Example 29, below.

Workup

custom10.98 g of a solid was collected

Sources & evidence

ORD record: ord-10ea3bd5204f49de986abbdae4752b28
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05464830

Linked notes

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