1,1-Dibromoethane → Methyl 8-methyl-2,3-dihydro-1,4-benzodioxin-6-carboxylate

HRID 642835Notes

Reaction equation

HRID 642835 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].Br[CH:21](Br)[CH3:22]>C(#N)C>[CH3:13][C:10]1[C:11]2[O:12][CH2:21][CH2:22][O:1][C:2]=2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=1

Participants

5

Reactant 3

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 68609716Methyl 3,4-dihydroxy-5-methylbenzoate

Product 1

HCID 45122025Methyl 8-methyl-2,3-dihydro-1,4-benzodioxin-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 34.0 g (0.19 mol) methyl 3,4-dihydroxy-5-methyl-benzoate, 77.12 g (0.56 mol) K2CO3 and 32.1 mL (0.37 mol) dibromoethane in 500 mL acetonitrile was refluxed for 6 h. The solid was filtered off, washed with 100 mL acetonitrile and the filtrate was evaporated to dryness i.vac. The residue was combined with 500 mL water and 500 mL EtOAc, the phases were separated, the organic phase was dried and evaporated to dryness i. vac. The residue was combined with 120 mL DIPE, the precipitate was suction filtered, washed with 50 mL DIPE and dried.

Workup

  1. temperaturewas refluxed for 6 h
  2. filtrationThe solid was filtered off
  3. washwashed with 100 mL acetonitrile
  4. customthe filtrate was evaporated to dryness i.vac
  5. customthe phases were separated
  6. customthe organic phase was dried
  7. customevaporated to dryness i
  8. filtrationfiltered
  9. washwashed with 50 mL DIPE
  10. customdried

Sources & evidence

ORD record
ord-a89cb0e2877f49738337f624419e08f9
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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