Acetic Anhydride → 3-(3-Acetoxy-4-acetyl-2-propylphenoxy)propylbromide

HRID 986707Notes

Reaction equation

HRID 986707 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH2:10][CH2:11][Br:12])=[C:6]([CH2:15][CH2:16][CH3:17])[C:5]=1[OH:18])(=[O:3])[CH3:2].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C(Cl)Cl.C(Cl)(Cl)Cl.CO>[C:35]([O:18][C:5]1[C:6]([CH2:15][CH2:16][CH3:17])=[C:7]([CH:13]=[CH:14][C:4]=1[C:1](=[O:3])[CH3:2])[O:8][CH2:9][CH2:10][CH2:11][Br:12])(=[O:37])[CH3:36]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanone

Product 1

HCID 201570243-(3-Acetoxy-4-acetyl-2-propylphenoxy)propylbromide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

In methylene chloride were dissolved 3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl bromide (2.8 g), triethylamine (6.2 ml) and dimethylaminopyridine (10 mg). To the solution was added dropwise acetic anhydride (4.2 ml) under ice-cooing. The reaction was allowed to proceed for 3 hours, and there was added methanol (5 ml). The mixture was left standing for 10 minutes. The solvent was evaporated off to leave syrup, which was dissolved in chloroform. The solution was washed with water, dried and concentrated. The resulting syrup was purified by means of a silica gel flash chromatography (chloroform) to give 3-(3-acetoxy-4-acetyl 2-propylphenoxy)propyl bromide (2.7 g) as colorless and transparent syrup.

Workup

  1. waitThe mixture was left
  2. waitstanding for 10 minutes
  3. customThe solvent was evaporated off
  4. customto leave syrup, which
  5. washThe solution was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting syrup was purified by means of a silica gel flash chromatography (chloroform)

Sources & evidence

ORD record
ord-975d3027e5684839aecf0a7925db8847
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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