Hydrochloric Acid → 1-Chloromethyl-5,8-dimethoxyisochroman

HRID 1833355Notes

Reaction equation

HRID 1833355 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[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])[CH:11]=[CH:10][C:9]=2[O:12][CH3:13])[CH2:5][CH2:6][O:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 121282-Chloro-1,1-diethoxyethaneHCID 819102,5-Dimethoxyphenethyl alcohol

Product 1

HCID 128284391-Chloromethyl-5,8-dimethoxyisochromanYield 105.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 10 g of 2,5-dimethoxyphenethyl alcohol and 10 g of chloroacetaldehyde diethyl acetal was added 14 ml of 10% hydrochloric acid and, after stirring at 80°-90° C for 1 hour, the reaction mixture was diluted with 100 ml of water and extracted with benzene. The extract was rinsed with water, dried and concentrated under reduced pressure. The residue was recrystallized from a solvent mixture of ether and petroleum ether. By the above procedure was obtained 14 g of 1-chloromethyl-5,8-dimethoxyisochroman as colorless needles, melting point: 101°-102° C.

Workup

  1. extractionextracted with benzene
  2. washThe extract was rinsed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from a solvent mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-d4f8919a891f48529dc4a14d96d6d7f1
Source dataset
uspto-grants-1978_01
Patent number
US04066648

Reaction notes

Loading…