Sulfuric Acid → ADONA

HRID 2407641Notes

Reaction equation

HRID 2407641 reaction equation
[K+].[Br-].CC1(C)N([O])C(C)(C)CCC1.[F:14][C:15]([F:35])([CH:18]([F:34])[O:19][C:20]([F:33])([F:32])[C:21]([F:31])([F:30])[C:22]([F:29])([F:28])[O:23][C:24]([F:27])([F:26])[F:25])[CH2:16][OH:17].[O-]Cl.[Na+].S(=O)(=O)(O)[OH:40]>CC#N.O>[F:14][C:15]([F:35])([CH:18]([F:34])[O:19][C:20]([F:33])([F:32])[C:21]([F:30])([F:31])[C:22]([F:28])([F:29])[O:23][C:24]([F:25])([F:26])[F:27])[C:16]([OH:40])=[O:17]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 253877Potassium BromideHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 866682301-Propanol, 2,2,3-trifluoro-3-[1,1,2,2,3,3-hexafluoro-3-(trifluoromethoxy)propoxy]-

Product 1

HCID 52915299ADONA

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The equipment of example 9 was used. 5.5 mL water, 20 ml MeCN, 0.36 g KBr, 0.12 g TEMPO (0.00077 mol) and 10 g 2,2,3-trifluoro-3-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-propan-1-ol were placed in the flask. 15% (wt) aq. NaOCl buffered to pH 8-9 (48 ml) were added via the dropping funnel in 3 portions during 18 hours of stirring at room temperature. Then concentrated sulphuric acid (1-2 ml 95%) were added to make the reaction mixture acidic. After extraction with diethyl ether, the organic phases were collected and dried over magnesium sulphate. The solvent was evaporated to give a colorless liquid (12.24 g), which was distilled using a water pump (15 mmHg, 92° C.) to give 8.54 g of pure acid. Yield: 82%.

Workup

  1. additionwere added via the dropping funnel in 3 portions during 18 hours
  2. extractionAfter extraction with diethyl ether
  3. customthe organic phases were collected
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-620b22d25499468085a85af40e0d347f
Source dataset
uspto-grants-2014_08
Patent number
US08809580B2

Reaction notes

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