Hydrochloric Acid → 1-(Chloromethyl)-6,7-dimethoxy-3,4-dihydro-1H-2-benzopyran

HRID 1833353Notes

Reaction equation

HRID 1833353 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][OH:8].C(O[CH:17](OCC)[CH2:18][Cl:19])C.Cl>O>[Cl:19][CH2:18][CH:17]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([O:12][CH3:13])[CH:10]=2)[CH2:6][CH2:7][O:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 121282-Chloro-1,1-diethoxyethaneHCID 819113,4-Dimethoxyphenethyl alcohol

Product 1

HCID 128284351-(Chloromethyl)-6,7-dimethoxy-3,4-dihydro-1H-2-benzopyran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 10 g. of 3,4-dimethoxyphenethylalcohol and 10 g. of chloroacetaldehyde diethyl acetal was added 14 ml of 10% hydrochloric acid. The mixture was stirred at 90° C for 10 minutes. After cooling, 100 ml of water was added to the reaction mixture, followed by extraction with benzene. The extract was rinsed with water, dried and concentrated under reduced pressure. By the above procedure was obtained 12 g of 1-chloromethyl-6,7-dimethoxyisochroman as an oil colored light-tan.

Workup

  1. additionTo a mixture of 10 g
  2. temperatureAfter cooling
  3. extractionfollowed by extraction with benzene
  4. washThe extract was rinsed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0cb4e64a86734e0c813f8397b0e4f09b
Source dataset
uspto-grants-1978_01
Patent number
US04066648

Reaction notes

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