Phosphoric Acid → 6-Hydroxy-7-tert.-butyl-2-methyl-2-cyanochromane

HRID 2286822Notes

Reaction equation

HRID 2286822 reaction equation
C(Cl)Cl.[C:4]([C:8]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:9]=1[OH:10])([CH3:7])([CH3:6])[CH3:5].[CH3:16][C:17](O)([C:20]#[N:21])[CH:18]=[CH2:19].P(=O)(O)(O)O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:10][C:9]1[CH:11]=[C:12]2[C:13](=[CH:14][C:8]=1[C:4]([CH3:7])([CH3:5])[CH3:6])[O:15][C:17]([CH3:16])([C:20]#[N:21])[CH2:18][CH2:19]2

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 6344DichloromethaneHCID 16043Tert-ButylhydroquinoneHCID 23317073Methylvinyl ketone cyanohydrin

Product 1

HCID 144156766-Hydroxy-7-tert.-butyl-2-methyl-2-cyanochromaneYield 30%

Reagents, catalysts & solvents 1

HCID 21584019Toluene ethylacetateSolvent

Procedure

Using the method described in the last paragraph of Example 1, but with methylene chloride instead of toluene, 56.0 g (0.338 mole) of tert.-butyl hydroquinone were reacted with 33.6 g (0.338 mole) of methyl vinyl ketone cyanohydrin, which was stabilized with 1 g of phosphoric acid. After chromatography of the crude product over silica gel, using toluene/ethyl acetate, 6-hydroxy-7-tert.-butyl-2-methyl-2-cyanochromane was obtained in 30% yield, as colorless crystals of melting point 153°-155° C.

Sources & evidence

ORD record
ord-bddf24b15c7b488fbb8eab64896a304a
Source dataset
uspto-grants-1981_05
Patent number
US04268446

Reaction notes

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