Pentachlorophenol → HCID 86733446, compound

HRID 1388095Notes

Reaction equation

[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[C:13]1([O:19][P:20]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl:35][C:36]1[C:41]([OH:42])=[C:40]([Cl:43])[C:39]([Cl:44])=[C:38]([Cl:45])[C:37]=1[Cl:46].[Al].[CH2:48]1[O:51][CH:49]1[CH3:50]>[Fe].C(N(CC)CC)C>[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[C:29]1([O:28][P:20]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Cl:35][C:36]1[C:41]([OH:42])=[C:40]([Cl:43])[C:39]([Cl:44])=[C:38]([Cl:45])[C:37]=1[Cl:46].[CH2:48]1[O:51][CH:49]1[CH3:50]

Participants

Conditions

Temperature: 140 °C

Procedure

A 1-liter flask, standardly equipped, was charged with 90 grams of dextrose and 85.2 grams of triphenylphosphite and heated to 140° C. 266 grams of pentachlorophenol containing about 750 ppm aluminum and iron compounds was added. Then propylene oxide was added dropwise with stirring at up to 150° C. After cooling, 4.5 grams of triethylamine was added and oxypropylation continued until the acid number was 0.3. The mixture was then stripped for 3 hours at 84°-88° C./1 mm. Hg. The 689 grams of oxypropylated product had the following properties.

Workup

customA 1-liter flask, standardly equipped
temperatureAfter cooling

Sources & evidence

ORD record: ord-e32eb0bff44047d38133910f3c82984b
Source dataset: uspto-grants-1984_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04430247

Reaction notes

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