Hydrochloric Acid → 1-Chloromethyl-5,6-dimethoxyisochroman

HRID 1833359Notes

Reaction equation

HRID 1833359 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][OH:7].C(O[CH:17](OCC)[CH2:18][Cl:19])C.Cl>O>[Cl:19][CH2:18][CH:17]1[C:8]2[C:4](=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[CH:10][CH:9]=2)[CH2:5][CH2:6][O:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 121282-Chloro-1,1-diethoxyethaneHCID 2656312-(2,3-Dimethoxyphenyl)ethanol

Product 1

HCID 128284361-Chloromethyl-5,6-dimethoxyisochromanYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30 g of 2,3-dimethoxyphenethyl alcohol, 30 g of chloroacetaldehyde diethyl acetal and 50 ml of concentrated hydrochloric acid was heated at 60°-80° C for 1 hour and, after cooling, the reaction mixture was diluted with water. The resultant oily precipitate was extracted into ethyl acetate, rinsed with water, dehydrated and concentrated under reduced pressure. The residue was then recrystallized from petroleum ether. By the above procedure was obtained 33 g of 1-chloromethyl-5,6-dimethoxyisochroman as colorless needles, melting point: 63°-65° C.

Workup

  1. temperaturewas heated at 60°-80° C for 1 hour
  2. temperatureafter cooling
  3. extractionThe resultant oily precipitate was extracted into ethyl acetate
  4. washrinsed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was then recrystallized from petroleum ether

Sources & evidence

ORD record
ord-129dc2f9b1d34e179c63c4a2886e147b
Source dataset
uspto-grants-1978_01
Patent number
US04066648

Reaction notes

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