Hydrochloric Acid → Methyl 2-(4-isopropoxyphenyl)acetate

HRID 9251

Reaction equation

HRID 9251 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:20]([CH3:22])[CH3:21].Cl>CN(C=O)C>[CH3:21][CH:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 525538Methyl 2-(4-isopropoxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl (4-hydroxyphenyl)acetate (1.0 g, 1.0 eq), Cs2CO3 (2.15 g, 1.1 eq) and 2-bromopropane (0.565 mL. 1.0 eq) were combined in 100 ml DMF at room temperature. The mixture was stirred overnight. The suspension was poured into 50 mL 1 N HCl and extracted with ethyl acetate. The organic phase was separated and washed with water followed by sodium bicarbonate. The organic phase was dried over sodium sulfate and the solvent was evaporated to give an oil. The resulting oil was chromatographed on silica gel using hexanes and ethyl acetate (95:5) to give methyl (4-(1-methylethoxy)phenyl)acetate.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customthe solvent was evaporated
  6. customto give an oil
  7. customThe resulting oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-7592862b4de4400099977859206fead8
Source dataset
uspto-grants-2006_08
Patent number
US07091230B2

Linked notes

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