Thionyl Chloride → 3-(Cyclopentyloxy)-4-methoxybenzoyl chloride

HRID 356911Notes

Reaction equation

HRID 356911 reaction equation
S(Cl)([Cl:3])=O.[CH:5]1([O:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=2[O:20][CH3:21])[C:14](O)=[O:15])[CH2:9][CH2:8][CH2:7][CH2:6]1>C1(C)C=CC=CC=1>[CH:5]1([O:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=2[O:20][CH3:21])[C:14]([Cl:3])=[O:15])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27793233-(Cyclopentyloxy)-4-methoxybenzoic acid

Product 1

HCID 27946003-(Cyclopentyloxy)-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

Stirring thionyl chloride (20 mL) is treated portionwise with 3-cyclopentyloxy-4-methoxybenzoic acid (5.0 g; that is prepared as described hereinbefore in Reference Example 2) and the solution is then heated at 85° C. for 3 hours. Toluene (50 mL) is added and the mixture is concentrated to give 3-cyclopentyloxy-4-methoxybenzoyl chloride (4.12 g) in the form of an oil which slowly crystallized. [NMR(CDCl3): 1.6-1.7 (m,2H),1.8-1.95(m,4H),1.94-2.05(m,2H),3.94(s,3H),4.85 (m,1H),6.9(d, 1H),7.55(d,1H),7.8(q,1H); Elemental analysis: C,61.3; H,5.94; Cl,13.9%; Calculated: C,61.3; H,5.94; Cl,13.92%].

Workup

  1. customthat is prepared
  2. concentrationthe mixture is concentrated

Sources & evidence

ORD record
ord-aa665ac68cbf4e76bf12e7462685082e
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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