Methanol → 3,4-Dihydro-5-methylnaphthalen-1(2H)-one

HRID 2402372Notes

Reaction equation

HRID 2402372 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6](C(O)=O)[CH:5]=[CH:4][C:3]1=2.S(=O)(=O)(O)O.[CH3:20]O>>[CH3:20][C:7]1[C:8]2[CH2:9][CH2:10][CH2:11][C:2](=[O:1])[C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 28184935-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 813573,4-Dihydro-5-methylnaphthalen-1(2H)-oneYield 87%

Conditions

Temperature
60 °C

Procedure

To a solution of 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (22.0 g, 116 mmol) in methanol (132 mL) was added sulfuric acid (22.7 g, 231 mmol) and the solution was heated to 60° C. for 4 h. Crystallization started when the solution was cooled, and then water (130 mL) was added. The slurry was filtered and the solid dried under vacuum to afford methyl 5-oxo-5,6,7,8-tetrahydronapthalene (20.6 g, 101 mmol, 87%) as an off-white solid. MS ESI calcd for C12H12O3 [M+H]+ 205, found 205.

Workup

  1. customCrystallization
  2. temperaturewas cooled
  3. additionwater (130 mL) was added
  4. filtrationThe slurry was filtered
  5. customthe solid dried under vacuum

Sources & evidence

ORD record
ord-7d614a4abbfd4f6eafe33661de4c4ec3
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Reaction notes

Loading…