Pentachlorophenol → HCID 131710245, compound

HRID 1388091Notes

Reaction equation

HRID 1388091 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 131710245HCID 131710245, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8471TriethylamineSolvent

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

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

Sources & evidence

ORD record
ord-c29daa84ee204d9e90e5722daaf3d95c
Source dataset
uspto-grants-1984_02
Patent number
US04430247

Reaction notes

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