Acetic Anhydride → HCID 59283848, compound

HRID 1641998Notes

Reaction equation

HRID 1641998 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:13][CH:14]=[CH2:15].[C:16](OC(=O)C)(=[O:18])[CH3:17]>N1C=CC=CC=1>[C:16]([O:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:13][CH:14]=[CH2:15])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54253994HCID 54253994, compound

Product 1

HCID 59283848HCID 59283848, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl 4-hydroxy-3-allyl-5-methylbenzoate (157 mg) in pyridine (5 mL) was cooled in an ice-bath under a nitrogen atmosphere and treated with acetic anhydride (1 mL). The reaction was stirred in the ice-bath for one hour and was then warmed to room temperature for 4 hours. The solvent was then removed under reduced pressure and the residue was suspended in anhydrous toluene (5-10 mL) and evaporated to dryness. The crude product was dissolved in ethyl acetate (30 mL) and washed with saturated aqueous ammonium chloride. It was then dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to give a brown oil. Yield=0.176 g (quantitative).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customevaporated to dryness
  3. dissolutionThe crude product was dissolved in ethyl acetate (30 mL)
  4. washwashed with saturated aqueous ammonium chloride
  5. dry with materialIt was then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customto give a brown oil

Sources & evidence

ORD record
ord-0d2960827cf6420bb99d0cb53d8717ef
Source dataset
uspto-grants-2012_02
Patent number
US08119422B2

Reaction notes

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