Triethyl phosphite → Benzoic acid, 4-((6-(diethoxyphosphinyl)hexyl)oxy)-, ethyl ester

HRID 2051753Notes

Reaction equation

HRID 2051753 reaction equation
[C:1]([C:6]1[CH:19]=[CH:18][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br)=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].[P:20]([O:27]CC)([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23]>[I-].[Na+]>[C:1]([C:6]1[CH:19]=[CH:18][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 18989362Ethyl p-(6-Bromohexyloxy)benzoate

Product 1

HCID 5271409Benzoic acid, 4-((6-(diethoxyphosphinyl)hexyl)oxy)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 5238Sodium IodideCatalyst

Procedure

[I; Ar is 4-C2H5OOCC6H4, Y is O(CH2)6, R is C2H5 ] was prepared from 15 g of 6-(4-carbethoxyphenoxy)hexyl bromide, 8.3 g of triethyl phosphite and a crystal of sodium iodide as a catalyst, according to the procedure of Example 1, and had the b.p. 190°-196° C. (0.2 mm); yield 9.5 g; MIC vs. herpes simplex type 2=6 mcg/ml. The IR and NMR spectra were consistent with the assigned structure.

Sources & evidence

ORD record
ord-5cceb62e2c63432f8def4f3d425f43e1
Source dataset
uspto-grants-1980_01
Patent number
US04182759

Reaction notes

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