Chloride → HCID 23227573, compound

HRID 361957Notes

Reaction equation

HRID 361957 reaction equation
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=[O:3].[OH:7][CH:8]([CH3:22])[CH2:9][C:10]([O:13][O:14][C:15]([CH3:21])([CH3:20])[CH2:16][CH:17]([OH:19])[CH3:18])([CH3:12])[CH3:11].[Cl-:23]>CC(OC)(C)C>[Cl:23][C:2]([C:1]([O:19][CH:17]([CH3:18])[CH2:16][C:15]([O:14][O:13][C:10]([CH3:12])([CH3:11])[CH2:9][CH:8]([O:7][C:1]([C:2]([Cl:4])=[O:3])=[O:5])[CH3:22])([CH3:20])[CH3:21])=[O:5])=[O:3]

Participants

5

Reactant 3

HCID 312ChlorideHCID 65578Oxalyl chlorideHCID 189864282-Pentanol, 4,4′-dioxybis[4-methyl-

Product 1

HCID 23227573HCID 23227573, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A 250 mL three-neck flask equipped with a magnetic stirrer, a thermometer and an addition funnel was charged with 50.8 g (400 mmoles) of oxalyl chloride and 75 mL of MTBE. Then to the resulting solution was slowly added 24.7 g (100 mmoles) of 95% di(3-hydroxy-1,1-dimethylbutyl) peroxide over a period of 30 minutes at 21°-30° C. The addition funnel was then replaced with a nitrogen gas tube and dry nitrogen gas wasslowly bubbled through the reaction mass in order to remove HCl over a period of 4 hours at 25°-30° C. The MTBE, excess oxalyl chloride, and any remaining gas were removed in vacuo using a water aspirator. Obtained was 38.2 g (97% of theory, uncorrected) of a amber liquid. An IR spectrum of the product showed no OH bands and showed a pairof carbonyl bands at 1790 cm-1 and 1755 cm-1. Based on hydrolyzable chloride content the assay of the product was 85.0% and the corrected yield was 82.7%.

Workup

  1. customA 250 mL three-neck flask equipped with a magnetic stirrer
  2. customof 30 minutes
  3. customat 21°-30° C
  4. customThe addition funnel was then replaced with a nitrogen gas tube
  5. customdry nitrogen gas wasslowly bubbled through the reaction mass in order
  6. customto remove HCl over a period of 4 hours at 25°-30° C
  7. customThe MTBE, excess oxalyl chloride, and any remaining gas were removed in vacuo
  8. customObtained

Sources & evidence

ORD record
ord-b74b2d0c28504ad8bb3f4f51cc0ec499
Source dataset
uspto-grants-1999_02
Patent number
US05866712

Reaction notes

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