Sulfuric Acid → HCID 57526216, compound
Reaction equation
C=C.[C:3]([CH2:16][C:17](I)([F:19])[F:18])([C:6]([C:9]([C:12]([F:15])([F:14])[F:13])([F:11])[F:10])([F:8])[F:7])([F:5])[F:4].CC1CC[C@@H]([C:28]([CH3:30])=C)CC=1.C(CC(CCI)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)(F)F.S(=O)(=O)(O)[OH:52]>>[C:3]([CH2:16][C:17]([CH2:30][CH2:28][OH:52])([F:19])[F:18])([C:6]([C:9]([C:12]([F:15])([F:14])[F:13])([F:11])[F:10])([F:8])[F:7])([F:5])[F:4]Participants
6
Conditions
- Temperature
- 240 °C
Procedure
C4F9CH2CF2CH2CH2OH was produced by introducing ethylene (25 g, 0.53 mol) was introduced to an autoclave charged with C4F9CH2CF2I (217 g, 0.87 mol) and d-(+)-limonene (1 g), and then the reactor was heated at 240° C. for 12 hours. Product was obtained via vacuum distillation 81˜91° C. at 19˜24 mmHg in 62% yield. Fuming sulfuric acid (70 mL) was added slowly to 50 g of C4F9CH2CF2CH2CH2I and mixture was stirred at 60° C. for 1.5 h. The reaction was quenched with ice-cold 1.5 wt % Na2SO3 aqueous solution and heated at 95° C. for 0.5 h. The bottom layer was separated and washed with 10 wt % aqueous sodium acetate and distilled to provide compound of formula C4F9CH2CF2CH2CH2OH: by 54-57° C. at 2 mmHg (267 Pascals).
Workup
- additionwas introduced to an autoclave
- customProduct was obtained via vacuum distillation 81˜91° C. at 19˜24 mmHg in 62% yield
- customThe reaction was quenched with ice-cold 1.5 wt % Na2SO3 aqueous solution
- temperatureheated at 95° C. for 0.5 h
- customThe bottom layer was separated
- washwashed with 10 wt % aqueous sodium acetate
- distillationdistilled
Sources & evidence
- ORD record
- ord-3441f8f421394d1284cdf0fad113b56f
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328317B2
Reaction notes
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