Sulfuric Acid → 2-Chloro-1-phenylethanol

HRID 2417348Notes

Reaction equation

HRID 2417348 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl-:9].[Na+].S(=O)(=O)(O)[OH:12].I([O-])(=O)(=O)=O.[Na+]>C(#N)C.O>[C:3]1([CH:2]([OH:12])[CH2:1][Cl:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 7501StyreneHCID 23667635Sodium periodate

Product 1

HCID 928982-Chloro-1-phenylethanolYield 95%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

Styrene (1 mmol) was treated with sodium chloride (1.2 mmol) in acetonitrile: water (2:1, 6 ml). 20% Sulfuric acid (5 ml) and sodium periodate (20 mol %) was added to the reaction mixture. The mixture was heated at 70° C. under inert atmosphere for 18 h. The product was purified by column chromatography to give 1-phenyl-2-chloroethanol (95%).

Workup

  1. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-8fe7ac3156164f4da33140b768551537
Source dataset
uspto-grants-2004_11
Patent number
US06825383B1

Reaction notes

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