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

HRID 2255136Notes

Reaction equation

HRID 2255136 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][OH:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(O[CH:17](OCC)[CH2:18][Cl:19])C.Cl>C(O)C>[Cl:19][CH2:18][CH:17]1[C:6]2[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11][CH2:12][O:13]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-benzopyranYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,4-dimethoxybenzeneethanol and 62,8 g of chloroacetaldehyde diethylacetal in 1 l of absolute ethanol saturated with anhydrous hydrochloric acid, was stirred at ambient temperature for 24 h. The solvent was evaporated and 88,4 g (88,8%) of 1-chloromethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran was obtained by distillation.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ac2e9b7b13634166a3f761891cb795ee
Source dataset
uspto-grants-1993_08
Patent number
US05238939

Reaction notes

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