Chloride → HCID 54394949, compound

HRID 36940Notes

Reaction equation

HRID 36940 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([OH:14])=O)[CH2:8][CH2:7][CH2:6]2.CN(C=O)C.[Cl-:20]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([Cl:20])=[O:14])[CH2:8][CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 312ChlorideHCID 6228DimethylformamideHCID 199365716-methoxy-2,3-dihydro-1H-indene-5-carboxylic acid

Product 1

HCID 54394949HCID 54394949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-methoxyindan-6-carboxylic acid (3.84 g), DMF (0.1 ml) and tetrahydrofuran (50 ml) was added oxyalyl chloride (2.1 ml) dropwise. The mixture was stirred at room temperature for 1 hour, at the end of which time the solvent was distilled off to give 5-methoxyindan-6-carboxylic acid chloride. This chloride was dissolved in dichloromethane (50 ml) and after addition of 2,6-di-tert-butylphenol (4.12 g), tin tetrachloride (2.6 ml) was added dropwise with ice-cooling. The mixture was stirred under ice-cooling for 30 minutes and, then, poured in diluted hydrochloric acid. The organic layer was washed with water and dried (MgSO4) and the solvent was distilled off. To the residue was added ethanol-hexane to give crystals of 5-(3,5-di-tert-butyl-4-hydroxybenzoyl)-6-methoxyindan (4.23 g, 55.7%). Recrystallization from ethanol gave colorless prisms, m.p. 154°-156° C.

Workup

  1. distillationwas distilled off

Sources & evidence

ORD record
ord-d9c47951809542d7a30d4adfcc60d349
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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