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

HRID 1281180Notes

Reaction equation

HRID 1281180 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]>>[Cl:17][CH2:10][C:9]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1

Participants

3

Reactant 2

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

Product 1

HCID 109007664-(Chloromethyl)-2-(cyclopentyloxy)-1-methoxybenzene

Conditions

Temperature
23 °C

Procedure

The toluene solution from Example 2 was cooled to 20° C. and concentrated hydrochloric acid (37.5%; 9.80 g) was added keeping the temperature between 20 and 22.7° C. A sample was taken 40 minutes after the addition was complete and analysed (GC) and the reaction was deemed to be complete. The phases were allowed to separate and the lower, aqueous phase discarded. Sodium bicarbonate (1.20 g) was charged to the reactor to neutralize the remaining hydrochloric acid. After stirring for 15 minutes the mixture was cooled to 23° C. and filtered to remove the solid (sodium bicarbonate, sodium chloride). A part of the toluene (17.07 g) was removed by distillation in vacuo (end of distillation: 28° C., 7 mbar).

Workup

  1. customthe temperature between 20 and 22.7° C
  2. additionafter the addition
  3. customto separate
  4. additionSodium bicarbonate (1.20 g) was charged to the reactor
  5. filtrationfiltered
  6. customto remove the solid (sodium bicarbonate, sodium chloride)
  7. customA part of the toluene (17.07 g) was removed by distillation in vacuo (end of distillation: 28° C., 7 mbar)

Sources & evidence

ORD record
ord-89f62a726f904db59c6e2af56aa7543f
Source dataset
uspto-grants-2002_09
Patent number
US06452022B1

Reaction notes

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