Ammonium Chloride → HCID 14822850, compound

HRID 1709162Notes

Reaction equation

HRID 1709162 reaction equation
[Li][CH3:2].[Li+].[Br-].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[O:14][CH2:13][C:12]([C:16]([OH:18])=O)([CH3:15])[O:11][C:10]=2[CH:19]=1.[NH4+].[Cl-]>C(OCC)C>[C:16]([C:12]1([CH3:15])[O:11][C:10]2[CH:19]=[C:6]([Cl:5])[CH:7]=[CH:8][C:9]=2[O:14][CH2:13]1)(=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 12637538HCID 12637538, compoundHCID 178419607HCID 178419607, compound

Product 1

HCID 14822850HCID 14822850, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

80 ml of a 2M MeLi-LiBr solution in ethyl ether was added dropwise, under nitrogen stream, to a solution of 17.7 g of (7-chloro-2,3-dihydro-2-methyl-1,4-benzodioxin-2-yl)carboxylic acid (prepared as described in Example 3) dissolved in 420 ml of anhydrous ethyl ether. The reaction mixture was refluxed for 1 hour, then poured into 200 ml of a NH4Cl saturated solution. The separated ether phase was washed with NaHCO3 and water, then dried. Solvent was removed under vacuum. After distillation, 2-acetyl-7-chloro-2,3-dihydro-2-methyl-1,4-benzodioxin (b.p. 168°-173° C. 0.6 mm Hg) was obtained.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. washThe separated ether phase was washed with NaHCO3 and water
  3. customdried
  4. customSolvent was removed under vacuum
  5. distillationAfter distillation

Sources & evidence

ORD record
ord-ff05cbd00fcf461aa01c63a4ae3ae81c
Source dataset
uspto-grants-1990_08
Patent number
US04948797

Reaction notes

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