Hydrochloric Acid → 6-(Hydroxymethyl)naphthalen-2-ol

HRID 1744184Notes

Reaction equation

HRID 1744184 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18](OC)=[O:19])[CH:12]=[CH:11]2.C1(C([O-])=O)C2C(=CC=CC=2)C=CC=1.Cl>O.C1COCC1>[OH:19][CH2:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:7])[CH:17]=[CH:16]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 390995Methyl 6-hydroxy-2-naphthoateHCID 50492651-NaphthoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 113327606-(Hydroxymethyl)naphthalen-2-olYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 3-necked, 1-L round bottomed flask equipped with an overhead stirrer, digital thermometer and 500-mL constant-pressure addition funnel with a nitrogen inlet was added 11 g (0.29 mol) of lithium aluminum hydride and 200 mL of anhydrous THF. The addition funnel was charged with a solution of 40 g (0.2 mol) of methyl 6-hydroxy-2-naphthoate. The flask was cooled in ice/water and the naphthoate slowly added over 1 hour. The suspension was stirred overnight, recooled and cautiously treated with 100 mL of water. The white suspension was poured into 5% (v/v) HCl and extracted several times with ethyl acetate. The combined extracts were washed with water, dried, evaporated and the residue recrystallized in hexane/ethyl acetate to yield a total of 30 g (87%) of the title compound in three crops as beige plates, mp 179–181° C.

Workup

  1. additiondigital thermometer and 500-mL constant-pressure addition funnel with a nitrogen inlet
  2. extractionextracted several times with ethyl acetate
  3. washThe combined extracts were washed with water
  4. customdried
  5. customevaporated
  6. customthe residue recrystallized in hexane/ethyl acetate

Sources & evidence

ORD record
ord-3fb71a3014eb4e2883f7ae50c654f8da
Source dataset
uspto-grants-2006_03
Patent number
US07014980B2

Reaction notes

Loading…