Tetrahydrofuran → HCID 68586097, compound

HRID 18060Notes

Reaction equation

HRID 18060 reaction equation
CS(C[C:6]1[CH:7]=[C:8]([CH2:12][OH:13])[CH:9]=[CH:10][CH:11]=1)(=O)=O.[CH3:14][S:15](CC1C=C(C=CC=1)C(O)=O)(=[O:17])=[O:16].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O1CCC[CH2:37]1>O.C(OCC)(=O)C>[CH3:14][S:15]([C:6]1[C:7]([CH3:37])=[C:8]([CH2:12][OH:13])[CH:9]=[CH:10][CH:11]=1)(=[O:17])=[O:16]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 49625833-(Methanesulfonylmethyl)benzoic acidHCID 17908456HCID 17908456, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 68586097HCID 68586097, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(3-Methylsulfonylmethylphenyl)methanol may be prepared by carrying out the procedure in the following manner: a mixture of 26 g of 3-(methylsulfonylmethyl)-benzoic acid and 4.6 g of lithium aluminum hydride in 600 cm3 of tetrahydrofuran is stirred for 18 hours at a temperature close to 20° C. The solution is cooled to 0° C. and then 15 cm3 of ethyl acetate, 30 cm3 of water, 5 cm3 of a 15% aqueous solution of sodium hydroxide and finally 30 cm3 of water are added-successively. The mixture is filtered on celite and the filtrate taken up in 600 cm3 of ethyl acetate. The organic phase is taken up in 500 cm3 of water and then 200 cm3 of a saturated aqueous sodium chloride solution, separated after settling, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). 10.4 g of (3-methylsulfonyl-methylphenyl)methanol are obtained in the form of a gum.

Workup

  1. customclose to 20° C
  2. filtrationThe mixture is filtered on celite
  3. custom200 cm3 of a saturated aqueous sodium chloride solution, separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-1b6b0f04f21e4f3b97941b6a3249547d
Source dataset
uspto-grants-2010_06
Patent number
US07741316B2

Reaction notes

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