4-(3-Chloro-4-octoxyphenyl)benzoyl chloride → Butyl (R)-2-(4-[4-(3-chloro-4-octyloxyphenyl)phenylcarbonyloxy]phenoxy)propanoate

HRID 1164771Notes

Reaction equation

HRID 1164771 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH:26][C:27]1[CH:42]=[CH:41][C:30]([O:31][C@H:32]([CH3:40])[C:33]([O:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:34])=[CH:29][CH:28]=1>C(O)CCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([O:26][C:27]3[CH:28]=[CH:29][C:30]([O:31][C@H:32]([CH3:40])[C:33]([O:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:34])=[CH:41][CH:42]=3)=[O:22])=[CH:19][CH:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 190242254-(3-Chloro-4-octoxyphenyl)benzoyl chlorideHCID 45108312(R)-Butyl 2-(4-hydroxyphenoxy)propanoate

Product 1

HCID 54561695Butyl (R)-2-(4-[4-(3-chloro-4-octyloxyphenyl)phenylcarbonyloxy]phenoxy)propanoateYield 15%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

This was prepared by the methods of Examples 2(b) and 2(c) using butanol instead of propanol and using 4-(3-chloro-4-octoxyphenyl)benzoyl chloride and Butyl (R)-2-(4-hydroxyphenoxy)propanoate (BHPP) in place of the OPBC and PHPTB used in Example 2(c), (yield 15%, SOR: +16°). The results of IR, 1H-NMR and mass spectroscopy and elemental analysis were consistent with the assigned structure.

Workup

  1. customused in Example 2(c), (yield 15%, SOR: +16°)
  2. customThe results of IR, 1H-NMR and mass spectroscopy and elemental analysis

Sources & evidence

ORD record
ord-1c4cc12767284f63b88dbba1b5afa74c
Source dataset
uspto-grants-1990_03
Patent number
US04906402

Reaction notes

Loading…