Sodium Sulfate → 2,5,7,8-Tetramethyl-6-hydroxy-2-(hydroxyethyl)chroman

HRID 1681292Notes

Reaction equation

HRID 1681292 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:26]([CH3:27])=[C:25]([CH3:28])[C:14]2[O:15][C:16]([CH2:20][C:21](OC)=[O:22])([CH3:19])[CH2:17][CH2:18][C:13]=2[C:12]=1[CH3:29])(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[OH:10][C:11]1[C:26]([CH3:27])=[C:25]([CH3:28])[C:14]2[O:15][C:16]([CH2:20][CH2:21][OH:22])([CH3:19])[CH2:17][CH2:18][C:13]=2[C:12]=1[CH3:29]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 14776652methyl 2-(6-acetoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)acetateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 118070842,5,7,8-Tetramethyl-6-hydroxy-2-(hydroxyethyl)chromanYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (LAH) (8.0 g) was suspended in ether (500 ml). A solution of methyl 2-(6-acetoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)acetate (12.16 g) in ether (200 ml) was added dropwise to the suspension. The mixture was stirred for 1 hour. A saturated aqueous solution of sodium sulfate was added dropwise to the reaction solution at room temperature to decompose excess LAH. The solution was filtered. The filtrate was evaporated to give the title compound (9.31 g) having the following physical data.

Workup

  1. filtrationThe solution was filtered
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5c4f5abd60d44089a6619aba7f8c5fc6
Source dataset
uspto-grants-1992_12
Patent number
US05169957

Reaction notes

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