HCID 18436361, compound → (1~4~,3~4~-Dimethoxy[2~3~,2~4~,2~5~,2~6~-tetrahydro-1~1~,2~1~:2~2~,3~1~-terphenyl]-2~4~,2~5~-diyl)dimethanol

HRID 351447Notes

Reaction equation

HRID 351447 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH:11]3[CH:15]([CH2:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:14](=O)[O:13][C:12]3=[O:27])=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:27][CH2:12][CH:11]1[CH:15]([CH2:14][OH:13])[CH2:16][C:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 18436361HCID 18436361, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18436365(1~4~,3~4~-Dimethoxy[2~3~,2~4~,2~5~,2~6~-tetrahydro-1~1~,2~1~:2~2~,3~1~-terphenyl]-2~4~,2~5~-diyl)dimethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To the cooled solution of 5,6-bis-(4-methoxy-phenyl)-3a,4,7,7a-tetrahydro-isobenzofuran-1,3-dione (2.95g) in THF (30 mL) at 0° C. was added LAH (1.0 M in THF, 20 mL) and the reaction mixture was stirred at 25° C. for 16. The reaction mixture was then quenched with methanol (20 mL) and aqueous HCl (10%, 30 mL) and then extracted with diethyl ether (2×300 mL). The organic layer was dried and concentrated to yield [6-Hydroxymethyl-3,4-bis-(4-methoxy-phenyl)-cyclohex-3-enyl]-methanol.

Workup

  1. customThe reaction mixture was then quenched with methanol (20 mL) and aqueous HCl (10%, 30 mL)
  2. extractionextracted with diethyl ether (2×300 mL)
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a284c620b48e4bbfaa0ccb0534fecb54
Source dataset
uspto-grants-2007_02
Patent number
US07183445B2

Reaction notes

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