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

HRID 345204
Notes
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Reaction equation

HRID 345204 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3283
Diethyl Ether
Solvent
2×

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-742d0e1ae1404a29b5261c7b150b2e7d
Source dataset
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05055598

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes