Oxalyl chloride → HCID 59752362, compound

HRID 1808002Notes

Reaction equation

HRID 1808002 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][C@H:9]([CH3:11])[CH2:8][CH2:7][C@H:6]1[C:12]([OH:14])=O)(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C)C=O>[C:1]([O:4][C@H:5]1[CH2:10][C@H:9]([CH3:11])[CH2:8][CH2:7][C@H:6]1[C:12]([Cl:18])=[O:14])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 57457642HCID 57457642, compound

Product 1

HCID 59752362HCID 59752362, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,2S,4R)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid (109 mg, 0.54 mmol) in dichloromethane (2.7 ml) was added oxalyl chloride (545 ul, 1.09 mmol) followed by 1 drop of dimethylformamide. The reaction mixture was stirred for 4 h at room temperature. The solvents were then removed to obtain 119 mg (99%) of (1R*,2S*,4R*)-2-Acetoxy-4-methyl-cyclohexanecarboxylic acid chloride.

Workup

  1. customThe solvents were then removed

Sources & evidence

ORD record
ord-64076f522c694225876d013d0659d4bb
Source dataset
uspto-grants-2013_01
Patent number
US08357718B2

Reaction notes

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