Oxalyl chloride → Hexahydro-2,5-methano-pentalene-3a-carbonyl chloride

HRID 255050

Reaction equation

HRID 255050 reaction equation
[CH2:1]1[CH:8]2[C:4]3([C:10]([OH:12])=O)[CH2:5][CH:6]([CH2:9][CH:2]1[CH2:3]3)[CH2:7]2.C(Cl)(=O)C([Cl:16])=O>ClCCl>[CH2:1]1[CH:8]2[C:4]3([C:10]([Cl:16])=[O:12])[CH2:5][CH:6]([CH2:9][CH:2]1[CH2:3]3)[CH2:7]2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 2733865Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acid

Product 1

HCID 13182402Hexahydro-2,5-methano-pentalene-3a-carbonyl chlorideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of commercially available hexahydro-2,5-methano-pentalene-3a-carboxylic acid (10 g, 0.06 mol) in dichloromethane (200 mL) was added oxalyl chloride (8.7 g, 0.066 mol). The mixture was stirred overnight and then concentrated under reduced pressure to afford the title compound as a colorless oil (11 g, 99%). MS (DCI/NH3) m/z 184 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-82faefc782d147d88966d283fa9acab9
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Linked notes

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