Hydrochloric Acid → HCID 11099403, compound

HRID 742100Notes

Reaction equation

HRID 742100 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]2[C:8](=[C:9]([Br:22])[CH:10]=[CH:11][C:12]=2[O:18][CH:19]([CH3:21])[CH3:20])[CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.Cl>C1COCC1>[Br:22][C:9]1[C:8]2[C:13](=[C:14]([O:16][CH3:17])[CH:15]=[C:6]([CH2:4][OH:3])[CH:7]=2)[C:12]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10970592HCID 10970592, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11099403HCID 11099403, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4.80 g (13.1 mmol) ethyl-8-bromo-5-isopropoxy-4-methoxy-2-naphthoate in 100 mL dry THF was cooled to 0° C. under Ar. A suspension of 498 mg (13.1 mmol) LiAlH4 in 60 mL dry THF was cooled to 0° C. and added to the ester over a period of 45 min. After stirring for 30 min at 0° C., 10 mL water and 10 mL 2N HCl were added carefully. The THF was concentrated in vacuo and the residue was extracted with dichloromethane, dried (MgSO4) and concentrated in vacuo. Column chromatography (dichloromethane/acetone, 95:5) afforded 4.00 g (95%) 1-bromo-7-hydroxymethyl-4-isopropoxy-5-methoxy-naphthalene as colorless needles (m.p. 120°-121° C.).

Workup

  1. concentrationThe THF was concentrated in vacuo
  2. extractionthe residue was extracted with dichloromethane
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0aab270578374d029489c763edda0df0
Source dataset
uspto-grants-1996_09
Patent number
US05552550

Reaction notes

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