Hydrochloric Acid → 4-(Chloromethyl)-2-(cyclopentyloxy)-1-methoxybenzene

HRID 842081Notes

Reaction equation

HRID 842081 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:10]O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:17]>C(Cl)Cl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:10][Cl:17])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 111387063-Cyclopentyloxy-4-methoxybenzyl alcohol

Product 1

HCID 109007664-(Chloromethyl)-2-(cyclopentyloxy)-1-methoxybenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-cyclopentyloxy-4-methoxybenzyl alcohol (112 g, 0.50 mol) prepared as described above, in 1 liter of methylene chloride was stirred at room temperature with concentrated HCl (110 ml, 1.2 mol) for 3 hours at which time the reaction was done by TLC. The layers were separated and the methylene chloride solution was washed twice with water and evaporated under reduced pressure to give 3-cyclopentyloxy-4-methoxybenzyl chloride (119 g, 100%).

Workup

  1. customThe layers were separated
  2. washthe methylene chloride solution was washed twice with water
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7c28d1695c92456bad9976215832185d
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

Loading…