Hydrochloric Acid → 3-(Cyclopentylthio)-4-methoxybenzoic acid

HRID 356941Notes

Reaction equation

HRID 356941 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH:19]1(Br)[CH2:23][CH2:22][CH2:21][CH2:20]1.Cl>CN(C)C=O.O>[CH:19]1([S:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=2[O:11][CH3:12])[C:5]([OH:7])=[O:6])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 124257504-Methoxy-3-sulfanylbenzoic acid

Product 1

HCID 211878613-(Cyclopentylthio)-4-methoxybenzoic acidYield 13.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 3-mercapto-4-methoxybenzoic acid (that is prepared as described in Reference Example 45 from 58 g of 3-chlorosulfonyl-4-methoxybenzoic acid) in dimethylformamide (400 mL) is treated with potassium carbonate (120 g) and cyclopentyl bromide (60 g). The solution is heated at 50° C. for 3 hours, and then it is cooled and poured into water (3 L) containing concentrated hydrochloric acid (250 mL). The resulting solid is filtered off and dried, to give 3-cyclopentylthio-4-methoxybenzoic acid (10.5 g), in the form of a white crude solid.

Workup

  1. temperatureit is cooled
  2. filtrationThe resulting solid is filtered off
  3. customdried

Sources & evidence

ORD record
ord-1bb07333b4034983ac4d9331d24a0b55
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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