Oxalyl chloride → HCID 68537219, compound

HRID 1992880Notes

Reaction equation

HRID 1992880 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([CH2:15][CH2:16][CH3:17])[CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][CH:8]=1.C(Cl)(=O)C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[C:12](=[O:14])[CH2:11][CH:10]([CH2:15][CH2:16][CH3:17])[CH2:9]2

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 685385143-{[3-(Methyloxy)phenyl]methyl}hexanoic acid

Product 1

HCID 68537219HCID 68537219, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-{[3-(Methyloxy)phenyl]methyl}hexanoic acid (92) (2.76 g, 11.7 mmol) was treated with oxalyl chloride followed by AlCl3 in CH2Cl2 to give 2.10 g (82%) of compound 93 as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ 0.90-1.00 (m, 3H), 1.35-1.50 (m, 4H), 2.10-2.35 (m, 2H), 2.60-2.75 (m, 2H), 2.90-3.00 (m, 1H), 3.85 (s, 3H), 6.65-6.70 (m, 1H), 6.82 (dd, J1=8.7 Hz, J2=1.4 Hz, 1H), 7.98 (d, J=8.8 Hz, 1H). LCMS (ESI): m/z 219 (M+H)+.

Sources & evidence

ORD record
ord-b3a11ffb75704e7483282da98e06cd4e
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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