Sulfuric Acid → 6-Chloro-3-methylnaphthalen-1-ol

HRID 926142Notes

Reaction equation

HRID 926142 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([CH3:16])=[CH:10][C:11]([O:13]CC)=O)[CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:11]([OH:13])=[CH:10][C:9]([CH3:16])=[CH:8]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 123861231HCID 123861231, compound

Product 1

HCID 896768476-Chloro-3-methylnaphthalen-1-ol

Conditions

Temperature
50 °C

Procedure

A flask containing the crude ethyl 4-(3-chlorophenyl)-3-methylbut-2-enoate (˜25 grams) was treated with concentrated H2SO4 (120 mL) and warmed to 50° C. for 2.5 h. The reaction was poured onto ˜500 mL of crushed ice. Once the ice had melted, the brown suspension was extracted with two portions of EtOAc (500 mL and 100 mL, respectively). The two extracts were combined, washed with saturated aq. NaHCO3, dried (MgSO4), filtered, and concentrated to ˜55 mL. The residue was treated with DCM and loaded onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product. 1H NMR (400 MHz, CDCl3) δ 8.07-8.05 (d, J=8.8 Hz, 1H), 7.69-7.68 (d, J=2.0 Hz, 1H), 7.35-7.32 (dd, J=2.0, 8.8 Hz, 1H); 7.12 (s, 1H); 6.65 (s, 1H); 5.21 (bs, 1H); 4.21-4.17 (dd, 2H); 2.41 (s, 3H).

Workup

  1. extractionthe brown suspension was extracted with two portions of EtOAc (500 mL and 100 mL
  2. washwashed with saturated aq. NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to ˜55 mL
  6. additionThe residue was treated with DCM
  7. custompurified by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2fe5590298834cb5aea30bf16952dbbc
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

Loading…