Diethyl Ether → 3-Amino-4-propoxybenzenemethanol

HRID 1606266Notes

Reaction equation

HRID 1606266 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[O:22][CH2:23][CH2:24][CH3:25])[C:16](O)=[O:17].C(OCC)C>[OH-].[K+].O>[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[O:22][CH2:23][CH2:24][CH3:25])[CH2:16][OH:17]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 1088073-Amino-4-propoxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 541824923-Amino-4-propoxybenzenemethanolYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

The preparation of part I of Example 1 was repeated with two major changes. The amounts of material employed were increased by a factor of about 10. The reduction in step (e) was carried out differently. To a solution of 1.1 g of lithium aluminum hydride (Alfa Inorganics-Ventron) in 50 ml of scrupulously dried tetrahydrofuran was added dropwise with stirring 2 g of 3-amino-4-n-propoxybenzoic acid in 100 ml of scrupulously dried tetrahydrofuran. The mixture was refluxed for 20 minutes, cooled, diluted with 1 ml of 15% potassium hydroxide and 3 ml of water. Then 150 ml of diethyl ether was added to extract the product. The ether extract was separated, dried and evaporated to yield 1.6 g of the 3-amino-4-n-propoxybenzyl alcohol product, mp 94°-95°.

Workup

  1. customThe preparation of part I of Example 1
  2. temperatureThe amounts of material employed were increased by a factor of about 10
  3. temperatureThe mixture was refluxed for 20 minutes
  4. temperaturecooled
  5. extractionto extract the product
  6. extractionThe ether extract
  7. customwas separated
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-fe689fd2d6284bbf9f5ee4d9073f2fe7
Source dataset
uspto-grants-1976_04
Patent number
US03952058

Reaction notes

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