Ammonium Chloride → HCID 70587015, compound

HRID 1112402Notes

Reaction equation

HRID 1112402 reaction equation
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15](C(O)=O)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]CCC.C[Li].[Cl-].[NH4+]>CCOCC>[CH3:3][CH2:4][CH2:5][CH:1]([O:11][C:12]1([C:1]([CH3:2])=[O:11])[CH:13]=[CH:14][CH:15]=[CH:19][CH2:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1385274-(Decyloxy)benzoic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 70587015HCID 70587015, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 27.8 g (0.1 mole) of 4-decyloxybenzoic acid and 300 ml of anhydrous ether stirred at room temperature is slowly added with stirring 100 ml of 2 M methyllithium in ether. The reaction mixture is stirred at room temperature for 2 hours then poured into 1 liter of a saturated ammonium chloride solution. The organic layer is separated, washed with 5% sodium bicarbonate and brine and evaporated to dryness to give a low melting solid which is recrystallized from hexane to give methyl 1-(4-decyloxy)phenyl ketone, M.P. 38°-39° C.

Workup

  1. additionis slowly added
  2. stirringThe reaction mixture is stirred at room temperature for 2 hours
  3. customThe organic layer is separated
  4. washwashed with 5% sodium bicarbonate and brine
  5. customevaporated to dryness
  6. customto give a low melting solid which
  7. customis recrystallized from hexane

Sources & evidence

ORD record
ord-f0b48bb843a34019aa1c6c1f274f0b0b
Source dataset
uspto-grants-1978_10
Patent number
US04122191

Reaction notes

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