Water → 1,3-Diphenoxypropan-2-yl acetate

HRID 1295542

Reaction equation

HRID 1295542 reaction equation
[OH:1][CH:2]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:19](Cl)(=[O:21])[CH3:20].C(N(CC)CC)C.O>O1CCCC1>[C:19]([O:1][CH:2]([CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 121401,3-Diphenoxy-2-propanol

Product 1

HCID 2430131,3-Diphenoxypropan-2-yl acetateYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.6 g (39.3 mmol) of 2-hydroxy-1,3-diphenoxypropane are dissolved in 80 ml of tetrahydrofurane (THF) and cooled by an ice bath. To the solution are added dropwise 6.8 g (86.4 mmol) of acetyl chloride and 6.0 g (59.0 mmol) of triethylamine successively. The reaction mixture is stirred at room temperature overnight, poured into 50 ml of water, and extracted with ethyl acetate. The organic phase is washed with water and brine, dried over MgSO4, and concentrated. The residue is purified by flash chromatography on silica gel with ethyl acetate and hexane (1:9) as eluent, yielding 5.1 g of 2-acetyloxy-1,3-diphenoxypropane as a colorless liquid.

Workup

  1. temperaturecooled by an ice bath
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography on silica gel with ethyl acetate and hexane (1:9) as eluent

Sources & evidence

ORD record
ord-732f28fd76fc4044b6c61066b793fed1
Source dataset
uspto-grants-2007_07
Patent number
US07244544B2

Linked notes

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