2-Chloropropionic acid → Propionic acid, 2-(4-(4-chlorobenzyl)phenoxy)-, (+-)-

HRID 1105667Notes

Reaction equation

HRID 1105667 reaction equation
Cl[CH:2]([CH3:6])[C:3]([OH:5])=[O:4].[OH-].[Na+].[Cl:9][C:10]1[CH:23]=[CH:22][C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1>O.C1(C)C(C)=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:2]([CH3:6])[C:3]([OH:5])=[O:4])=[CH:17][CH:16]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 117342-Chloropropionic acidHCID 14798Sodium HydroxideHCID 131220024-[(4-Chlorophenyl)methyl]phenol

Product 1

HCID 3054672Propionic acid, 2-(4-(4-chlorobenzyl)phenoxy)-, (+-)-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7237O-XyleneSolvent

Procedure

129.8 Parts of 2-chloropropionic acid, 194 parts of 50% sodium hydroxide solution and 80 parts of water are mixed as described in Example 1. The clear, viscous liquid so obtained is added portionwise to a solution of 218.5 parts of 4-(4'-chlorobenzyl)-phenol in 1,000 parts of xylene; the reaction temperature being maintained at 110°-115° C. by azeotropic distillation of water in a water trap. The addition being complete, stirring is continued for 15 minutes at 110° C. Work-up is as described in Example 2. 290.5 Parts of 2-[4'-(4"-chlorobenzyl)-phenoxy]-propionic acid are obtained. The content of pure final product is 99.8%, corresponding to a yield of 99.8% of theory. The residual content of 4-(4'-chlorobenzyl)--phenol is 0.1%.

Workup

  1. customThe clear, viscous liquid so obtained
  2. additionThe addition

Sources & evidence

ORD record
ord-5415978fe9d4462d9a44c06e7ee5b5f1
Source dataset
uspto-grants-1982_01
Patent number
US04309547

Reaction notes

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