Oxalyl chloride → 2-[3-(Phenylmethoxy)phenyl]acetyl Chloride

HRID 2114734Notes

Reaction equation

HRID 2114734 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH2:15][C:16]([O:18]CC3C=CC=CC=3)=O)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+].C1(COC2C=C(CC(O)=O)C=CC=2)C=CC=CC=1.C(Cl)(=O)C([Cl:50])=O>O.ClCCl.CN(C=O)C.C1COCC1.O>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH2:15][C:16]([Cl:50])=[O:18])[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 65578Oxalyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 4592030(3-Benzyloxyphenyl)acetic acidHCID 15470856Benzyl 2-(3-(benzyloxy)phenyl)acetate

Product 1

HCID 118178352-[3-(Phenylmethoxy)phenyl]acetyl ChlorideYield 99%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of phenylmethyl 2-[3-(phenylmethoxy)phenyl]acetate (9.97 g, 0.03 mol) in a 5:1 mixture of THF/water was added a solution of lithium hydroxide monohydrate (2.5 g, 0.06 mol) in water. The reaction was allowed to stir at 50° C. for 6 hours and then at room temperature overnight. Solvent was removed and the reaction was acidified with 4 N HCl solution while on ice. 2-[3-(Phenylmethoxy)phenyl]acetic acid precipitated from the solution and was collected by filtration. The 2-[3-(phenylmethoxy)phenyl]acetic acid (7.0 g, 0.03 mol) was dissolved in dichloromethane (100 ml) and a small amount of DMF (4 drops) was added. To the reaction was added oxalyl chloride (5.23 ml, 0.06 mol). The reaction was allowed to stir for 6 hours, and solvents were removed to yield the title compound (7.7 g, 99% yield): ES-MS (m/z) 386 [M+H]+.

Workup

  1. customat room temperature
  2. customovernight
  3. customSolvent was removed
  4. custom2-[3-(Phenylmethoxy)phenyl]acetic acid precipitated from the solution
  5. filtrationwas collected by filtration
  6. stirringto stir for 6 hours
  7. customsolvents were removed

Sources & evidence

ORD record
ord-7955573cfe2745a69b43b4b4fa77d99e
Source dataset
uspto-grants-2008_10
Patent number
US07435729B2

Reaction notes

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