Isopropanol → HCID 480254, compound

HRID 1653930Notes

Reaction equation

HRID 1653930 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].C(O)(C)C.[Cl-].[Na+]>CCOCC>[CH3:17][C:16]1[C:8]([OH:7])=[C:9]([CH2:10][OH:11])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 5234Sodium ChlorideHCID 67383-Methylsalicylic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 480254HCID 480254, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

4.9 mmol of lithium aluminum hydride are placed, under a nitrogen atmosphere, in 50 ml of ether. 3.3 mmol of 2-hydroxy-3-methylbenzoic acid, in solution in 40 ml of ether, are added dropwise while maintaining a reflux for 4 hours. The mixture is then cooled on ice and 12.5 ml of isopropanol and then 7.5 ml of a saturated sodium chloride solution are added. After 10 hours at room temperature, the mixture is filtered, rinsed with 1N hydrochloric acid and extracted with ether. The product is then obtained after silica column purification, using as eluent a pentane/ethyl acetate mixture (7/3).

Workup

  1. temperaturewhile maintaining
  2. temperaturea reflux for 4 hours
  3. filtrationthe mixture is filtered
  4. washrinsed with 1N hydrochloric acid
  5. extractionextracted with ether
  6. customThe product is then obtained
  7. customafter silica column purification

Sources & evidence

ORD record
ord-84cd4f891e4e4b168498664b6330168f
Source dataset
uspto-grants-1995_04
Patent number
US05403953

Reaction notes

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