7-Methoxynaphthalene-1-carboxylic acid → 1-Hydroxymethyl-7-Methoxynaphthalene

HRID 889676Notes

Reaction equation

HRID 889676 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C:13](O)=[O:14])=[CH:5][CH:4]=1.B.C1COCC1>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][OH:14])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 3482947-Methoxynaphthalene-1-carboxylic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 154530791-Hydroxymethyl-7-MethoxynaphthaleneYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-2 °C

Procedure

To 1 equivalent of 7-methoxy-1-naphthoic acid (100 g) in THF (3.8 ml/g) there are slowly added 2.5 equivalents of 1M BH3-THF (1.235 liters). During the addition, the temperature of the reaction mixture is maintained at 5° C. (+/−2° C.) and then the mixture is left at ambient temperature for 3 hours. After evaporation under reduced pressure, the residue is taken up in dichloromethane and washed with water. The organic phase is dried over MgSO4 and then the solvents are evaporated off under reduced pressure to yield the title compound in the form of a light-brown solid in a yield of 91%.

Workup

  1. additionDuring the addition
  2. customAfter evaporation under reduced pressure
  3. washwashed with water
  4. dry with materialThe organic phase is dried over MgSO4
  5. customthe solvents are evaporated off under reduced pressure

Sources & evidence

ORD record
ord-c0f429a22e3242c7b0b7e9007dc9d02d
Source dataset
uspto-grants-2012_08
Patent number
US08252951B2

Reaction notes

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