8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic Acid → 1-(8-Methoxy-1,2,3,4-tetrahydronaphth-2-yl)methanol

HRID 963994Notes

Reaction equation

HRID 963994 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([C:13](O)=[O:14])[CH2:9][CH2:8]2.B.CSC>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 36247098-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic AcidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 190790161-(8-Methoxy-1,2,3,4-tetrahydronaphth-2-yl)methanolYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (5 g) in tetrahydrofuran (50 ml) was brought to reflux temperature under nitrogen and borane-dimethyl sulphide complex (10M solution in dimethyl sulphide; 5 ml) was added dropwise. The mixture was then heated under gentle reflux for 5 hours, allowed to stand at ambient temperature for 16 hours, then cooled in ice and quenched by the cautious addition of water. The mixture was then acidified by the addition of 5M hydrochloric acid, heated to drive off dimethyl sulphide, cooled, basified by the addition of aqueous sodium hydroxide solution (5M), and the product extracted into ethyl acetate. The extracts were washed with water, dried over magnesium sulphate, and the solvents were removed to leave 1-(8-methoxy-1,2,3,4-tetrahydronaphth-2-yl)methanol as a pale yellow syrup (3.8 g), which solidified slowly at ambient temperature.

Workup

  1. temperatureto reflux temperature under nitrogen
  2. temperatureThe mixture was then heated
  3. temperatureunder gentle reflux for 5 hours
  4. temperaturecooled in ice
  5. customquenched by the cautious addition of water
  6. additionThe mixture was then acidified by the addition of 5M hydrochloric acid
  7. temperatureheated
  8. temperaturecooled
  9. additionbasified by the addition of aqueous sodium hydroxide solution (5M)
  10. extractionthe product extracted into ethyl acetate
  11. washThe extracts were washed with water
  12. dry with materialdried over magnesium sulphate
  13. customthe solvents were removed

Sources & evidence

ORD record
ord-2464725dd35a465a88eb6a1503d5681d
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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