Dichloromethane → 1,2,3,4-Tetrahydro-8-methyl-1-naphthalenemethanol

HRID 729774Notes

Reaction equation

HRID 729774 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([C:12](O)=[O:13])[CH2:9][CH2:8][CH2:7]2.ClCCl>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([CH2:12][OH:13])[CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 12778763HCID 12778763, compound

Product 1

HCID 118052711,2,3,4-Tetrahydro-8-methyl-1-naphthalenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-Methyl-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid (J. Org. Chem. 1982, 47, 2590-2593) (0.066 g, 0.34 mmol) was dissolved in tetrahydrofuran (3 mL). To the solution was then added at 0° C. a 1.0M solution of borane-methyl sulfide complex in dichloromethane (0.7 mL, 0.69 mmol). The reaction mixture was stirred at room temperature for 15 minutes, refluxed for 2 hrs, then cooled down to 0° C. and quenched with methanol. The solvent was then evaporated in vacuo to yield a crude oil. The crude oil was partitioned with water and diethyl ether. The organic layer was dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield crude (8-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol as an oil which was used directly to the next step.

Workup

  1. temperaturerefluxed for 2 hrs
  2. temperaturecooled down to 0° C.
  3. customquenched with methanol
  4. customThe solvent was then evaporated in vacuo
  5. customto yield a crude oil
  6. customThe crude oil was partitioned with water and diethyl ether
  7. dry with materialThe organic layer was dried with Na2SO4
  8. filtrationfiltered
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-0899306fd8b74cb4a68aec38acf29d53
Source dataset
uspto-grants-2009_09
Patent number
US07582649B2

Reaction notes

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