Hydrochloric Acid → HCID 10977112, compound

HRID 1262678Notes

Reaction equation

HRID 1262678 reaction equation
[CH3:1][C@@H:2]1[C:11](=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4][C@H:3]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(O)(=O)C.[Zn]>[CH3:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4][C@H:3]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12753184(2R,3S)-3-Methyl-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one

Product 1

HCID 10977112HCID 10977112, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Trans-3-methylflavanone (3.50 g.) was dissolved in acetic acid (120 ml) and concentrated hydrochloric acid (15 ml) and the solution added to amalgamated zinc prepared from zinc powder (25.0 g) and mercuric chloride (1.0 g). The mixture was stirred for 1 hr. at room temperature, then allowed to stand at room temperature for a further 16 hr. The zinc residue was filtered off, washing with acetic acid, and the filtrate and washings diluted with water and extracted with toluene. The extract was washed with saturated sodium bicarbonate solution, dried, and evaporated. The residue was recrystallised from methanol three times to yield the required trans-3-methylflavan (1.00 g., m.pt. 77°-78°). The configuration was confirmed by 1H n.m.r.

Workup

  1. customat room temperature
  2. waitto stand at room temperature for a further 16 hr
  3. filtrationThe zinc residue was filtered off
  4. washwashing with acetic acid
  5. additionthe filtrate and washings diluted with water
  6. extractionextracted with toluene
  7. washThe extract was washed with saturated sodium bicarbonate solution
  8. customdried
  9. customevaporated
  10. customThe residue was recrystallised from methanol three times

Sources & evidence

ORD record
ord-0c9d7340f2a14283b757a5fd8c379ee8
Source dataset
uspto-grants-1984_06
Patent number
US04452991

Reaction notes

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