Methyl chloroformate → 2-Methyl-1-naphthol
Reaction equation
C1(O)C2C(=CC=CC=2)C=CC=1.[OH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[C:23](O)=O.ClC(OC)=O.[BH4-].[Na+]>C1COCC1.C(N(CC)CC)C>[CH3:23][C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]=1[OH:12]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
1-naphthol (5) was heated with twice its weight of KHCO3 at 200° C. for 5 hours (stainless steel bomb) whereby 1-hydroxy-2-naphthoic acid (9) was obtained in a yield of 60%. 1-Hydroxy-2-naphthoic acid (9) was treated with methyl chloroformate and triethylamine in THF, followed by sodium borohydride reduction, whereby 2-methyl-naphthol (I) was produced in a yield of 80%.
Workup
- customwas obtained in a yield of 60%
Sources & evidence
- ORD record
- ord-9268980dbcd94c068c537f2d13247f9b
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05420362
Reaction notes
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