Ammonium Chloride → 1-(6-Methoxy-2-naphthyl)heptan-1-ol

HRID 1866467

Reaction equation

HRID 1866467 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=[O:14])[CH:7]=[CH:6]2.[CH2:15]([Mg]Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[NH4+].[Cl-]>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([OH:14])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 769916-Methoxy-2-naphthaldehydeHCID 178444609HCID 178444609, compound

Product 1

HCID 223273441-(6-Methoxy-2-naphthyl)heptan-1-olYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a 3-neck flask equipped with an overhead stirrer, dropping funnel and thermometer was added 6-methoxy-2-naphthaldehyde (70.760 g, 380 mmol) and Et2O (1400 mL). The stirred suspension under N2 was cooled in an ice bath followed by the slow addition of hexylmagnesium bromide (228 mL of a 2 M solution in Et2O) over 1 h. Temperature was kept below 12° C. After the addition, the reaction was stirred for 3 h at room temperature then cooled in an ice bath and slowly quenched w/saturated aq. NH4Cl (250 mL). After quenching, the ice bath was removed and the mixture was stirred for a half-hour then diluted with H2O (750 mL) to dissolve all solids. The layers were separated and the aqueous layer extracted with Et2O (3×200 mL). The combined organics were washed with water (3×200 mL), and brine (2×200 mL), dried over Na2SO4, filtered, rotovap'd and dried in vacuo to give the desired product as an off-white solid (101.1 g, 371.2 mmol, 98%) with mp 71-74° C. 15 g of crude alcohol was recrystallized from hexane to give the desired product as a white solid (11.7 g) with mp 71-73° C.; 1H NMR (DMSO-d6) δ 0.82 (t, J=6.7 Hz, 3H), 1.15-1.38 (m, 8H), 1.58-1.71 (m, 2H) 3.85 (s, 3H), 4.58-4.64 (m, 1H), 5.14 (d, J=4.3 Hz, 1H), 7.12 (dd, J=2.6, 9.0 Hz, 1H), 7.26 (d, 2.4 Hz, 1H), 7.42 (dd, J=1.5, 8.4 Hz, 1H), 7.70 (s, 1H), 7.74 (d, J=8.6 Hz, 1H), 7.77 (d, J=8.9 Hz, 1H), IR (solid) 3280, 2920, 2860, 1610, 1270, 1170, 1040, and 860 cm−1; mass spectrum [ESI], m/z 255 (MH-H2O)+;

Workup

  1. customTo a 3-neck flask equipped with an overhead stirrer
  2. temperatureThe stirred suspension under N2 was cooled in an ice bath
  3. customwas kept below 12° C
  4. additionAfter the addition
  5. temperaturethen cooled in an ice bath
  6. customAfter quenching
  7. customthe ice bath was removed
  8. stirringthe mixture was stirred for a half-hour
  9. additionthen diluted with H2O (750 mL)
  10. dissolutionto dissolve all solids
  11. customThe layers were separated
  12. extractionthe aqueous layer extracted with Et2O (3×200 mL)
  13. washThe combined organics were washed with water (3×200 mL), and brine (2×200 mL)
  14. dry with materialdried over Na2SO4
  15. filtrationfiltered
  16. customdried in vacuo

Sources & evidence

ORD record
ord-800da9578a194d7ca03dbc372da5a2a0
Source dataset
uspto-grants-2009_12
Patent number
US07629377B2

Linked notes

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