Hydrochloric Acid → (1,4-Dimethoxynaphthalen-3-yl)methanol

HRID 430925Notes

Reaction equation

HRID 430925 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([O:19][CH3:20])=[CH:11][C:10]=1[C:21](OC)=[O:22].[NH4+].[Cl-].Cl>CCOCC.C1COCC1.CO>[CH3:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([O:19][CH3:20])=[CH:11][C:10]=1[CH2:21][OH:22]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 3859696Methyl 1,4-dimethoxy-2-naphthoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10704023(1,4-Dimethoxynaphthalen-3-yl)methanolYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of lithium aluminum hydride (29.2 mL, 29.2 mmol, 1 M in ether) in ether (30 mL) was heated to reflux under argon. A solution of ester 22 (7.18 g, 29.2 mmol) in ether (30 mL) and THF (8 mL) was added dropwise over 35 min via an addition funnel. The milky yellow mixture was refluxed for 3 h and then cooled to 0° C. Methanol (10 mL) was added dropwise and the resulting clear yellow solution was stirred for 1 h. Saturated NH4Cl (20 mL) and aqueous HCl (5 mL, 10%) were added and the mixture was extracted with ether (6×). The combined organic layers were washed with saturated Na2CO3 (2×) and H2O (2×), dried (MgSO4), filtered and evaporated. Column chromatography of the crude product (35:65 EtOAc:hexanes) afforded 23a (5.82 g, 92%) as a pink solid; Rf=0.48 (35:65 EtOAc:hexanes); mp=69-70° C.; lit mp=68-70° C.25; 1H NMR (CDCl3): δ 8.23 (dd, 1H), 8.03 (dd, 1H), 7.52 (m, 2H), 6.82 (s, 1H), 4.89 (s, 2H), 3.99 (s, 3H), 3.92 (s, 3H), 1.95 (bs, 1H).

Workup

  1. temperatureto reflux under argon
  2. temperatureThe milky yellow mixture was refluxed for 3 h
  3. extractionthe mixture was extracted with ether (6×)
  4. washThe combined organic layers were washed with saturated Na2CO3 (2×) and H2O (2×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c4a3216418e94295951b4e8415e3f4fe
Source dataset
uspto-grants-2003_12
Patent number
US06656926B2

Reaction notes

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