Carbamate → 2-Methyl-1-naphthol

HRID 37686

Reaction equation

HRID 37686 reaction equation
ClC(OCC)=O.[OH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:18](O)=O.C(=O)([O-])N.[BH4-].[Na+]>O1CCCC1.O.C(N(CC)CC)C>[CH3:18][C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[OH:7]

Participants

8

Reactant 4

HCID 276CarbamateHCID 68441-Hydroxy-2-naphthoic acidHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydride

Product 1

HCID 240552-Methyl-1-naphtholYield 69.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Minami et al (Chem. Pharm. Bull., 27(3), 816-820, 1979) disclose the following reaction scheme: ethyl chloroformate was added, at a temperature of 0°-5° C. and over a period of 1 hour, to a solution of 1-hydroxy-2-naphthoic acid and triethylamine in tetrahydrofuran whereby the correspondence carbamate was produced. The reaction mixture was added to a solution of sodium borohydride in water, with stirring, at a temperature of 5° to 15° C., and over a period of 1 hour. Extraction with ether gave 2-methyl-1-naphthol in a yield of 69.2%.

Workup

  1. customthe following reaction scheme
  2. customwas produced
  3. extractionExtraction with ether

Sources & evidence

ORD record
ord-bfb307b5515741e097ed404e6b01c0f2
Source dataset
uspto-grants-1995_05
Patent number
US05420362

Linked notes

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