Tetrahydrofuran → 6-(Hydroxymethyl)naphthalen-2-ol

HRID 720804Notes

Reaction equation

HRID 720804 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[OH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C:23](OC)=[O:24])[CH:17]=[CH:16]2.C1(C([O-])=O)C2C(=CC=CC=2)C=CC=1>O>[OH:24][CH2:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([OH:12])[CH:22]=[CH:21]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 390995Methyl 6-hydroxy-2-naphthoateHCID 50492651-NaphthoateHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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) HCI 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. additionThe white suspension was poured into 5% (v/v)
  3. extractionand extracted several times with ethyl acetate
  4. washThe combined extracts were washed with water
  5. customdried
  6. customevaporated
  7. customthe residue recrystallized in hexane/ethyl acetate

Sources & evidence

ORD record
ord-fc4b9e455b45478bbdb510d8f2d18ff7
Source dataset
uspto-grants-2006_11
Patent number
US07135595B2

Reaction notes

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