Pentachlorophenol → Alpha-Methylglucoside Triethylphosphite Pentachlorophenol Propylene Oxide

HRID 2419174Notes

Reaction equation

HRID 2419174 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

8

Reactant 5

HCID 992PentachlorophenolHCID 6378Propylene Oxide2×HCID 31215Triethyl phosphiteHCID 64947methyl alpha-D-glucopyranosideHCID 5359268Aluminum

Product 1

HCID 131710245Alpha-Methylglucoside Triethylphosphite Pentachlorophenol Propylene Oxide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8471TriethylamineSolvent

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° l 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

  1. customA 5-liter flask, standardly equipped
  2. temperatureheated to 122° l C
  3. custom/2 mm. Hg to remove volatiles

Sources & evidence

ORD record
ord-12dbb43515344a3a990082c486e49127
Source dataset
uspto-grants-1978_08
Patent number
US04105597

Reaction notes

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