Pentachlorophenol → Alpha-Methylglucoside Triethylphosphite Pentachlorophenol Propylene Oxide

HRID 1448841Notes

Reaction equation

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

Participants

Conditions

Temperature: 122 °C

Procedure

A 5-liter flask, standardly equipped, was charged with 776 grams of alpha-methylglucoside, 1264 grams of pentachlorophenol containing about 750 ppm of aluminum and iron compounds, 240 grams of triethylphosphite, and heated to 122° C. 1025 ml. of propylene oxide was added at 122°-138° C. over a 6-hour period. Then 48 grams of triethylamine was added, followed by 265 ml. more of propylene oxide to reduce the acid number to less than 1. The mixture was then stripped for 2 hours at 80°-85° C./2 mm. Hg to remove volatiles. The oxypropylated product weighed 3827 grams and analyzed as follows:

Workup

customA 5-liter flask, standardly equipped
custom/2 mm. Hg to remove volatiles

Sources & evidence

ORD record: ord-0cb3c3fa5c6d4c2eb5a68c5fa9c59443
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04187357

Reaction notes

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