(4-Chlorophenyl)acetic acid → 6-Chloro-2-(4-chlorophenyl)hexanoic acid

HRID 1803190Notes

Reaction equation

HRID 1803190 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26]I>>[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 15880(4-Chlorophenyl)acetic acidHCID 825271-Chloro-4-iodobutaneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 581101096-Chloro-2-(4-chlorophenyl)hexanoic acidYield 90.7%

Procedure

Step AH (1): 2-(4-Chlorophenyl)acetic acid (2.5 g, 14.65 mmol) was deprotonated with NaHMDS (1.0 M in THF, 29.3 mL, 29.3 mmol) and reacted with 1-chloro-4-iodobutane (1.80 mL, 14.7 mmol) using a procedure analogous to Step AC (1) to afford 6-chloro-2-(4-chlorophenyl)hexanoic acid (3.47 g, 59% yield). LC-MS (M−H)− 259.1.

Sources & evidence

ORD record
ord-d30373d31e294df88d4716266f7eee27
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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