Dimethylformamide → 4-Benzyloxy-3-methoxyphenylacetyl chloride

HRID 467036

Reaction equation

HRID 467036 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](O)=[O:17])=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:24])=O.CN(C=O)C>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([Cl:24])=[O:17])=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2979644-Benzyloxy-3-methoxyphenylacetic Acid

Product 1

HCID 110982704-Benzyloxy-3-methoxyphenylacetyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyloxy-3-methoxyphenylacetic acid (5.0 g, 18 mmol), from Step 2, in THF (40 mL) was added oxalyl chloride (2.54 g, 20 mmol, 1.1 equivalent) followed by a catalytic amount of DMF (~0.2 mL). The resulting mixture was stirred at ambient temperature for 2 hours and then concentrated under reduced pressure to give the title compound which was used without purification.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf89bfaa21a34cfb920a433345c7f7c1
Source dataset
uspto-grants-1992_10
Patent number
US05158948

Linked notes

Loading…