Oxalyl chloride → 2,3-Dihydro-6-methoxy-1H-indene-1-carbonyl chloride

HRID 1032262Notes

Reaction equation

HRID 1032262 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[C:12]([OH:14])=O)=[CH:5][CH:4]=1.C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[C:12]([Cl:18])=[O:14])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 30471416-Methoxy-2,3-dihydro-1H-indene-1-carboxylic acid

Product 1

HCID 148226062,3-Dihydro-6-methoxy-1H-indene-1-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

6-Methoxy-indane-1-carboxylic acid, 6.0 g (31 mmol), a compound of Formula 3, was dissolved in 50 ml of methylene chloride and reacted at ambient temperature with 4.0 ml (46 mmol) of oxalyl chloride in the presence of one drop of DMF. After 2 hours, the reaction mixture was brought to reflux and maintained for 15 minutes. It was then concentrated under vacuum and stirred for about 30 minutes, yielding 6-methoxy-indane-1-carboxylic acid chloride, which was sufficiently pure to be used for the next step.

Workup

  1. temperatureto reflux
  2. temperaturemaintained for 15 minutes
  3. concentrationIt was then concentrated under vacuum

Sources & evidence

ORD record
ord-1dd86bb3526441e782fc016bbe0fa7f7
Source dataset
uspto-grants-1990_09
Patent number
US04957914

Reaction notes

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