Water → Rac.-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetonitrile

HRID 1701296Notes

Reaction equation

HRID 1701296 reaction equation
[CH3:1]/[C:2](=[CH:6]/[CH2:7][C:8]1[C:13]([O:14]C(=O)C)=[C:12]([CH3:18])[C:11]([CH3:19])=[C:10]([O:20]C(=O)C)[C:9]=1[CH3:24])/[CH2:3][C:4]#[N:5].C=C(CCC1C(OC(=O)C)=C(C)C(C)=C(OC(=O)C)C=1C)CC#N.C[O-].[Na+].O>CO.CCOCC>[OH:20][C:10]1[C:11]([CH3:19])=[C:12]([CH3:18])[C:13]2[O:14][C:2]([CH3:1])([CH2:3][C:4]#[N:5])[CH2:6][CH2:7][C:8]=2[C:9]=1[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 10942334Sodium MethoxideHCID 203337993-Methylene-5-(2,4,5-trimethyl-3,6-diacetyloxy-phenyl)pentanenitrileHCID 20333801Z-3-methyl-5-(2,4,5-trimethyl-3,6-diacetyloxyphenyl)-3-pentenenitrile

Product 1

HCID 20333800Rac.-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A slurry of 500 mg (1.52 mmoles) of the mixture of E-and Z-3-methyl-5-(2,4,5-trimethyl-3,6-diacetyloxyphenyl)-3-pentenenitrile and 3-methylene-5-(2,4,5-trimethyl-3,6-diacetyloxy-phenyl)pentanenitrile in 5 ml of methanol was treated with 0.71 ml (3.34 mmoles) of a 4.7 M methanolic sodium methoxide solution. The resulting mixture was stirred at room temperature for 4.5 hr, then poured into 20 ml of water and worked-up with ether in the usual manner affording 345 mg (93%) of rac. 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetonitrile as a tan solid.

Sources & evidence

ORD record
ord-9ec8b0f0858a4b03a66b38a4d8f20d24
Source dataset
uspto-grants-1980_03
Patent number
US04192816

Reaction notes

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