Ammonium Chloride → HCID 20439315, compound

HRID 1995883Notes

Reaction equation

HRID 1995883 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]([OH:14])=O)[CH2:4][CH2:3]1.[CH3:16][Li].[Cl-].[NH4+]>CCOCC>[CH3:15][C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12](=[O:14])[CH3:16])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 204393164,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-carboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 20439315HCID 20439315, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

16.8 g of 1,1-dimethyl-tetralin-4-carboxylic acid are treated dropwise in 200 ml of absolute ether under a nitrogen or argon atmosphere with 99.2 ml of a 2 molar solution of methyl lithium in ether (198.4 mmol). The mixture is stirred at room temperature for 1 hour and subsequently held at reflux temperature for a further 1 hour. The mixture is poured into saturated ammonium chloride solution, extracted with ether, washed neutral with water and dried over sodium sulphate. The ether is evaporated and the residue is fractionally distilled. There are obtained 8.4 g of 1,1-dimethyl-4-acetyl-tetralin of boiling point 69° C./0.07 mmHg; nD20 =1.5333; yield 50%. Odour: see (5).

Workup

  1. temperatureat reflux temperature for a further 1 hour
  2. extractionextracted with ether
  3. washwashed neutral with water
  4. dry with materialdried over sodium sulphate
  5. customThe ether is evaporated
  6. distillationthe residue is fractionally distilled

Sources & evidence

ORD record
ord-0d483d8fa1fd4725b458570d689412c5
Source dataset
uspto-grants-1983_09
Patent number
US04406828

Reaction notes

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