Hydrochloric Acid → HCID 23447970, compound

HRID 1840308Notes

Reaction equation

HRID 1840308 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH:6](O)[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[ClH:21]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH:6]([Cl:21])[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11043648HCID 11043648, compound

Product 1

HCID 23447970HCID 23447970, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-methoxy-α-(1-naphthyl)benzyl alcohol (2.5 g, 9.5 mmol) in diethyl ether (5 mL) was added 35% hydrochloric acid (10 mL) at 0° C. The reaction mixture was warmed to r.t. in 1 h, and then extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with aqueous NH4Cl solution and brine, dried over MgSO4. Evaporation of solvents gave 3-methoxy-α-(1-naphthyl)benzyl chloride (1.94 g, 72%). GC-MS (Rt=10.30 min) 282 (M+), 247, 232,215, 202, 189, 163, 151, 139, 123, 101.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic layers were washed with aqueous NH4Cl solution and brine
  3. dry with materialdried over MgSO4
  4. customEvaporation of solvents

Sources & evidence

ORD record
ord-1bb82ea615834daeaf076256a706f5ab
Source dataset
uspto-grants-2004_01
Patent number
US06680321B1

Reaction notes

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