Acetone → 2-Acetoxyphenoxyethyl Alcohol

HRID 1060260Notes

Reaction equation

HRID 1060260 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11].[CH3:12][C:13](C)=[O:14].C(=O)([O-])[O-].[K+].[K+].C(OC(=O)C)(=O)C>C(Cl)Cl.CO>[C:13]([O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][OH:1])(=[O:14])[CH3:12]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 785192-(2-Hydroxyethoxy)phenol

Product 1

HCID 113215132-Acetoxyphenoxyethyl Alcohol

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

2-(2-Hydroxyethoxy)phenol (308 g; 2 mol) was taken up in a 5 L Erlnmeyer flask fitted with mechanical stirrer. Anhydrous acetone (4 L, dried over K2CO3), and potassium carbonate powder (290 g; 2.1 mol) were added, and the mixture was stirred vigourously. Acetic anhydride (207 mL; 2.2 mol) was added from an additional funnel slowly over a period of 1 hour. Stiiring was continued for 3 hours. TLC (CH2Cl2/MeOH : 9:1, v/v) showed disapperence of starting material. The reaction mixture was filtered, solid washed thoroughly with acetone (1 L). The combined fractions was concentrated and purified by chromatography eluting with hexane and ethyl acetate (0% to 35% EtOAc; v/v). The product was obtained as a colorless viscous oil. Yield 258-264 gms (70-72%)

Workup

  1. customfitted with mechanical stirrer
  2. filtrationThe reaction mixture was filtered
  3. washsolid washed thoroughly with acetone (1 L)
  4. concentrationThe combined fractions was concentrated
  5. custompurified by chromatography
  6. washeluting with hexane and ethyl acetate (0% to 35% EtOAc; v/v)
  7. customThe product was obtained as a colorless viscous oil

Sources & evidence

ORD record
ord-09ce5d67459e4e4e8a8f4960917c0b2d
Source dataset
uspto-grants-2003_02
Patent number
US06521775B2

Reaction notes

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