Toluene → 5,7-Dimethylchroman-2-one

HRID 1761655Notes

Reaction equation

HRID 1761655 reaction equation
C(C1[C:5]([OH:17])=[CH:6][C:7]2CCCC(CCC)C=2C=1)(=O)C.C12CC3CC(CC(C3)C1=[O:28])C2.N1[CH2:33][CH2:32][CH2:31][CH2:30]1.[C:34]1([CH3:40])[CH:39]=CC=C[CH:35]=1>>[CH3:30][C:31]1[CH:35]=[C:34]([CH3:40])[CH:39]=[C:33]2[C:32]=1[CH2:7][CH2:6][C:5](=[O:17])[O:28]2

Participants

5

Reactant 4

HCID 1140TolueneHCID 31268PyrrolidineHCID 64151AdamantanoneHCID 212421503-Acetyl-5-propyl-5,6,7,8-tetrahydro-2-naphthol

Product 1

HCID 126604295,7-Dimethylchroman-2-one

Procedure

3-Acetyl-5-propyl-5,6,7,8-tetrahydro-2-naphthol (1) was reacted with adamantanone and pyrrolidine in toluene to give the corresponding derivative of the Example 2 compound (2) which was hydrolysed, with methanol containing a few drops of conc. hydrochloric acid, to the chromanone (3). Reduction of the chromanone (3) (2.7 g) with sodium borohydride (0.7 g) in methanol, gave the chromanol (4) (2.7 g), which was dehyrated by heating with anhydrous copper sulphate (1 g) to yield the product (5) colourless crystals from methanol (1.8 g).

Sources & evidence

ORD record
ord-87cee2dc7aaa4484a65cc7844dd1961e
Source dataset
uspto-grants-1989_05
Patent number
US04826977

Reaction notes

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