Pentachlorophenol → HCID 86733445, compound

HRID 1388094Notes

Reaction equation

[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]([Cl:11])[C:3]=1[Cl:12].[Al].[C:14]1([O:20][P:21]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[CH2:43]1[O:46][CH:44]1[CH3:45]>[Fe].C(N(CC)CC)C>[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]([Cl:11])[C:3]=1[Cl:12].[C:30]1([O:29][P:21]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[CH2:43]1[O:46][CH:44]1[CH3:45]

Participants

Conditions

Temperature: 125 °C

Procedure

A 5-liter flask, standardly equipped, was charged with 1330 grams of pentachlorophenol containing about 750 ppm of aluminum and iron compounds, 500 grams of triphenylphosphite and 232.5 grams of aniline. After heating to approximately 125° C., 750 ml. of propylene oxide was added at a temperature up to 150° C. The mixture was then cooled and 35 grams of triethylamine added, followed by oxypropylation at approximately 90° C. until steady refluxing. The product was then stripped for 2 hours at 80°-82° C./1-2 mm. Hg. The 2931 grams of oxypropylated product had the following properties.

Workup

customA 5-liter flask, standardly equipped
temperatureThe mixture was then cooled
customfollowed by oxypropylation at approximately 90° C. until steady refluxing

Sources & evidence

ORD record: ord-717f92eab5a5418195cad1c5ef706255
Source dataset: uspto-grants-1984_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04430247

Reaction notes

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