Hydrochloric Acid → HCID 20211049, compound

HRID 1906877Notes

Reaction equation

HRID 1906877 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([CH2:11][OH:12])[CH2:8][CH2:7][C:6]=2[CH:13]=1.[Cu][C:15]#[N:16].CN(C)C=O.Cl>[Fe](Cl)Cl.O>[OH:12][CH2:11][CH:9]1[CH2:8][CH2:7][C:6]2[CH:13]=[C:2]([C:15]#[N:16])[CH:3]=[CH:4][C:5]=2[O:10]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 202110506-Bromo-3,4-dihydro-2H-1-benzopyran-2-methanolHCID 178418546HCID 178418546, compound

Product 1

HCID 20211049HCID 20211049, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 297 parts of 6-bromo-3,4-dihydro-2H-1-benzopyran-2-methanol and 108 parts of copper (I) cyanide in 450 parts of N,N-dimethylformamide was stirred and refluxed for 4 hours. The reaction mixture was poured onto a solution of 600 parts of iron chloride in 180 parts of hydrochloric acid and 1000 parts of water. The whole was stirred for 20 minutes at 60° C. The aqueous phase was extracted with methylbenzene. The extract was filtered over Hyflo. The filtrate was washed successively with 10% hydrochloric acid, water, 10% sodium hydroxide and again with water, filtered again, dried and evaporated, yielding 112 parts (49.3%) of 3,4-dihydro-2-(hydroxymethyl)-2H-1-benzopyran-6-carbonitrile; mp. 85° C. (intermediate 2).

Workup

  1. temperaturerefluxed for 4 hours
  2. stirringThe whole was stirred for 20 minutes at 60° C
  3. extractionThe aqueous phase was extracted with methylbenzene
  4. filtrationThe extract was filtered over Hyflo
  5. washThe filtrate was washed successively with 10% hydrochloric acid, water, 10% sodium hydroxide and again with water
  6. filtrationfiltered again
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-64f223ea570b43beb78791b6924bf85b
Source dataset
uspto-grants-1987_03
Patent number
US04654362

Reaction notes

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