Methanol → 7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 643901

Reaction equation

HRID 643901 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].[NH4+].[Cl-].C[OH:18]>>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([OH:18])[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 25517Ammonium ChlorideHCID 744146-MethoxytetralinHCID 4311764Sodium borohydride

Product 1

HCID 230252467-Methoxy-1,2,3,4-tetrahydronaphthalen-2-ol

Conditions

Temperature
-20 °C

Procedure

A solution of 7-methoxy-3,4-dihydro-1H-naphthalene (5.00 g, 28.4 mmol) in MeOH (5 mL) is added to a suspension of NaBH4 (2.8 g, 74 mmol) in MeOH (40 mL) at −20° C. The mixture is stirred at −20° C. for 10 min. Solid NH4Cl is added, and the mixture is concentrated to remove most of the MeOH. The residue is partitioned between EtOAc and, sequentially, aq. NH4Cl and brine. The organic layer is dried over MgSO4 and concentrated to afford 7-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol as a red solid.

Workup

  1. concentrationthe mixture is concentrated
  2. customto remove most of the MeOH
  3. customThe residue is partitioned between EtOAc
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b0fdc90f0edb422d89e00836ca254aa7
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Linked notes

Loading…