Chloroform → HCID 20223012, compound

HRID 979813Notes

Reaction equation

HRID 979813 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10]C=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[Cl:13]OC(C)(C)C.[CH:19]([Cl:22])(Cl)Cl>>[Cl:13][C:3]1[C:2]([OH:1])=[C:19]([Cl:22])[CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:12]

Participants

4

Reactant 3

HCID 6212Chloroform2×HCID 521297Tert-Butyl hypochloriteHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 20223012HCID 20223012, compoundYield 96%

Procedure

A solution of 6-hydroxy-1-tetralone (1.62 g) in chloroform (100 ml) was treated with t-butyl hypochlorite (2.3 ml) dropwise at room temperature. After 1.5 hours the reaction was diluted with chloroform and quenched with aqueous sodium bisulfite. The organic layer was separated, washed with brine, dried and evaporated in vacuo affording the desired product in 96% yield. Recrystallized from hot ethyl acetate yielded (1 g) of needles.

Workup

  1. customquenched with aqueous sodium bisulfite
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c994e4600eab49bab3ac4ccd21f39ae0
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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