Water → [3,4-Bis(methoxymethoxy)]phenacyl chloride

HRID 379840

Reaction equation

HRID 379840 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([OH:12])[C:8](=[CH:10][CH:11]=1)[OH:9])=[O:4].Cl[CH2:14][O:15][CH3:16].C(N(CC)CC)C.O.[O:25]1[CH2:29]CC[CH2:26]1>>[CH3:14][O:15][CH2:16][O:12][C:7]1[CH:6]=[C:5]([CH:11]=[CH:10][C:8]=1[O:9][CH2:26][O:25][CH3:29])[C:3](=[O:4])[CH2:2][Cl:1]

Participants

6

Reactant 5

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 668342-Chloro-3',4'-dihydroxyacetophenone

Product 1

HCID 18367805[3,4-Bis(methoxymethoxy)]phenacyl chlorideYield 78%

Procedure

4-(Chloroacetyl)catechol (4.1 g, 22 mmol), chloromethylmethylether (3.7 ml, 44 mmol) and triethylamine (12 ml) in tetrahydrofuran (50 ml) were stirred together for 1 h, the mixture poured into water (80 ml) and extracted with diethyl ether (80 ml×2). The organic extract was washed consecutively with 2N aqueous sodium hydroxide (50 ml×2) and water (50 ml), dried (MgSO4), and solvent evaporated to give 4.7 g (78%) of the title compound as a pale brown solid. (The crude product was used in the next step without further purification.)

Workup

  1. extractionextracted with diethyl ether (80 ml×2)
  2. extractionThe organic extract
  3. washwas washed consecutively with 2N aqueous sodium hydroxide (50 ml×2) and water (50 ml)
  4. dry with materialdried (MgSO4), and solvent
  5. customevaporated

Sources & evidence

ORD record
ord-3d5e3b655e424d4fa7c337ff821b9190
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Linked notes

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