Water → 6-(2-Chloroethyl)-4-methoxy-2H-1,3-benzodioxole

HRID 1253103Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][CH2:13]O)[CH:6]=[C:7]2[O:11][CH2:10][O:9][C:8]=12.N1C=CC=CC=1.S(Cl)([Cl:23])=O.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][CH2:13][Cl:23])[CH:6]=[C:7]2[O:11][CH2:10][O:9][C:8]=12

Participants

Conditions

Temperature: 60 °C

Procedure

3.92 g (20 mmol) of 2-(3-methyoxy-4,5-methylenedioxyphenyl)ethyl alcohol (3) and 1.94 ml (24 mmol) of pyridine were dissolved in 40 ml of toluene, and to this mixture was added portionwise 1.74 ml (24 mmol) of thionyl chloride in 5 ml of toluene under cooling with water. The mixture was heated to 60° C. for 2 hours, then cooled and washed with 30 ml of water, 20 ml of water, 30 ml of a saturated sodium hydrocarbonate aqueous solution and 30 ml of a saturated saline solution successively in this order. This reaction mixture was then dried over anhydrous sodium sulfate and decolored by active carbon. The solvent was distilled off to obtain 4.05 g of 2-(3-methoxy-4,5-methylenedioxyphenyl)ethyl chloride (5) as a crystal with a yield of 94%, which was recrystallized from n-hexane. Melting point: 67°-68° C.

Workup

temperaturecooled
washwashed with 30 ml of water, 20 ml of water, 30 ml of a saturated sodium hydrocarbonate aqueous solution and 30 ml of a saturated saline solution successively in this order
dry with materialThis reaction mixture was then dried over anhydrous sodium sulfate and decolored by active carbon
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-423b504fdab24c618ba631a744a3dcbe
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04746747

Reaction notes

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