Sulfuric Acid → HCID 131730680, compound

HRID 473120Notes

Reaction equation

HRID 473120 reaction equation
COCCOC.[BH4-].[Na+].[C:9]([CH:13]([O:15][C:16]([C:19]([C:22]([C:25]([C:28]([C:31](OC)=[O:32])([F:30])[F:29])([F:27])[F:26])([F:24])[F:23])([F:21])[F:20])([F:18])[F:17])[F:14])([F:12])([F:11])[F:10].S(=O)(=O)(O)O>O>[C:9]([CH:13]([O:15][C:16]([C:19]([C:22]([C:25]([C:28]([CH2:31][OH:32])([F:29])[F:30])([F:27])[F:26])([F:24])[F:23])([F:21])[F:20])([F:18])[F:17])[F:14])([F:12])([F:11])[F:10]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 80711,2-DimethoxyethaneHCID 4311764Sodium borohydrideHCID 131730681HCID 131730681, compound

Product 1

HCID 131730680HCID 131730680, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A 5-L round-bottom flask equipped with a mechanical stirrer and nitrogen bubbler was charged with 1 L of 1,2-dimethoxyethane and sodium borohydride (76 grams, 2.0 moles) and heated to 80° C. CF3CFH—O—(CF2)5COOCH3 (713 grams, 1.67 mole), prepared as described in Part A, was added to the stirred slurry over a period of one hour. A mixture of concentrated sulfuric acid (198 grams) and water (1.0 L) was added to the reaction mixture. The lower phase was separated, and the solvent was removed by distillation. Further distillation provided 506 grams of CF3CFH—O—(CF2)5CH2OH (boiling point 173° C.), the structure of which was confirmed by Fourier Transform Infrared Spectroscopy (FTIR) and 1H and 19F Nuclear Magnetic Resonance (NMR) Spectroscopy.

Workup

  1. customA 5-L round-bottom flask equipped with a mechanical stirrer
  2. additionwas added to the stirred slurry over a period of one hour
  3. additionwas added to the reaction mixture
  4. customThe lower phase was separated
  5. customthe solvent was removed by distillation
  6. distillationFurther distillation

Sources & evidence

ORD record
ord-21f1a9ef3af44b5b880116ce063494bd
Source dataset
uspto-grants-2014_01
Patent number
US08633288B2

Reaction notes

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