Pivalic acid → 8-Methoxy-1,2-dihydro-benzo[f]chromen-3-one

HRID 1648102Notes

Reaction equation

HRID 1648102 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.CC[C:16](CC)=[C:17]([C:20]([O-])([O-])[O-:21])CC.CC(C)(C)C(O)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]1[CH2:16][CH2:17][C:20](=[O:21])[O:13][C:8]=1[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 6417Pivalic acidHCID 2886346-Methoxy-2-naphtholHCID 19600934Triethyl orthoacrylate

Product 1

HCID 199219128-Methoxy-1,2-dihydro-benzo[f]chromen-3-oneYield 86.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Starting with a solution of 6.29 g (36.1 mmol) of 6-methoxy-2-naphthalenol, 12.58 g (72.2 mmol) of triethyl orthoacrylate and 1.84 g (18.1 mmol) of trimethylacetic acid in 70 mL of toluene, the title compound (7.12 g; 86.4%) was obtained as a white solid, mp 122°-123° C., using the procedure of example 220.

Sources & evidence

ORD record
ord-dc8c7e1948d440919f383c1b9c4af8a8
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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