Triclosan → 5-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-2,2-dimethylbutyrate

HRID 279911

Reaction equation

[CH:1]1[C:6]([Cl:7])=[CH:5][C:4]([OH:8])=[C:3]([O:9][C:10]2[CH:11]=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=2[Cl:16])[CH:2]=1.[CH3:18][C:19]1([CH3:27])[CH2:25][CH2:24][C:23](=[O:26])[O:22][C:20]1=[O:21]>C(N(CC)CC)C>[C:23]([CH2:24][CH2:25][C:19]([CH3:27])([CH3:18])[C:20]([O:8][C:4]1[CH:5]=[C:6]([Cl:7])[CH:1]=[CH:2][C:3]=1[O:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=1[Cl:16])=[O:21])([OH:26])=[O:22]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of triclosan (29.0 g.), triethylamine (15 ml.) and 2,2-dimethylglutaric anhydride (20 g.) was heated at 80° C. for 5 hours. A further quantity (2.0 g.) of anhydride and triethylamine (1 ml.) were added and heating continued for 24 hours. The mixture was cooled to ambient temperature, washed with 2M hydrochloric acid (100 ml.), then with water (3×80 ml.) and dried (MgSO4). The solution obtained was evaporated. The brown residual oil was dissolved in hot cyclohexane. The solution on cooling gave white crystals which were recrystallised from cyclohexane/petrol 60-80 to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-2,2-dimethylbutyrate (C') (12.7 g.), m.p. 125°-128° C.

Workup

temperatureheating
temperatureThe mixture was cooled to ambient temperature
washwashed with 2M hydrochloric acid (100 ml.)
dry with materialwith water (3×80 ml.) and dried (MgSO4)
customThe solution obtained
customwas evaporated
dissolutionThe brown residual oil was dissolved in hot cyclohexane
temperatureThe solution on cooling
customgave white crystals which
customwere recrystallised from cyclohexane/petrol 60-80

Sources & evidence

ORD record: ord-d097fe9abe56492db156157af1bcf77c
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587262

Linked notes

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