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28940-11-6

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28940-11-6 Usage

Uses

7-Methyl-2H-1,5-benzodioxepin-3(4H)-one has shown gender-specific reduction in overall olfactory impact of stress-related odor by cross adaptation in human apocrine secretion.

Description

Watermelon Ketone, also known as calone or methylbenodioxepinone is a hydrocarbon compound with similar structure of certain alicyclic C11-hydrocarbons such as ectocarpene. It is a flavor and fragrance chemical compound with special odorant. It was used as a scent component since the 1980s for its watery, fresh, ozone accords. It was later supplemented into several perfumes of the marine trend, beginning in the 1990s.

Chemical Properties

Watermelon Ketone is a white powder with a fresh marine odor, mp 35–41°C. It is used to create fresh aquatic marine notes in perfume oils for many applications, for example, for fine fragrances, soaps, and shower gels.

Preparation

The material is prepared by etherification of 4-methylpyrocatechol with two equivalents of alkyl 2-bromoacetate and subsequentDieckmann condensation followed by hydrolysis and decarboxylation.

Flammability and Explosibility

Nonflammable

Trade name

Aquamor (Aromor), Calone? (Firmenich), Ganone (Agan).

References

https://www.parchem.com/chemical-supplier-distributor/Watermelon-Ketone-015008.aspx https://en.wikipedia.org/w/index.php?title=Calone&oldid=568553437 https://www.perfumersworld.com/product/calone-1YG00077

Check Digit Verification of cas no

The CAS Registry Mumber 28940-11-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,9,4 and 0 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 28940-11:
(7*2)+(6*8)+(5*9)+(4*4)+(3*0)+(2*1)+(1*1)=126
126 % 10 = 6
So 28940-11-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O3/c1-7-2-3-9-10(4-7)13-6-8(11)5-12-9/h2-4H,5-6H2,1H3

28940-11-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Watermelon Ketone

1.2 Other means of identification

Product number -
Other names Watermelonketonecalone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:28940-11-6 SDS

28940-11-6Synthetic route

7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxolane]
1323441-46-8

7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxolane]

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With sulfuric acid In acetone for 6h; Reagent/catalyst; Solvent; Reflux;95%
7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-one oxime

7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-one oxime

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With sodium nitrite In water; acetonitrile at 40℃; for 10h;94%
(±)-7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-ol
944558-65-0

(±)-7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-ol

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate for 2.5h;87%
Reaxys ID: 11944038

Reaxys ID: 11944038

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With sodium carbonate; potassium iodide In acetone for 4h; Heating / reflux;84.45%
1,3-Dichloroacetone
534-07-6

1,3-Dichloroacetone

4-methyl-1,2-dihydroxybenzene
452-86-8

4-methyl-1,2-dihydroxybenzene

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With sodium carbonate; potassium iodide In butanone for 4.16667h; Heating / reflux;76.24%
With sodium carbonate; potassium iodide In cyclohexanone for 4.41667h; Heating / reflux;75.25%
With sodium carbonate; potassium iodide In acetone for 12h; Heating / reflux;59.91%
1,3-dibromoroacetone
816-39-7

1,3-dibromoroacetone

4-methyl-1,2-dihydroxybenzene
452-86-8

4-methyl-1,2-dihydroxybenzene

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With sodium carbonate; potassium iodide In acetone for 12h; Heating / reflux;69.95%
2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester
52589-39-6

2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
Stage #1: 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.5h; Dieckmann cyclisation;
Stage #2: With hydrogenchloride In ethanol; water for 0.0666667h; microwave irradiation;
Stage #1: 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.5h;
Stage #2: With hydrogenchloride In ethanol at 90℃; for 2h; Further stages.;
0.59 g
Stage #1: 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.5h; Dieckmann Condensation; Inert atmosphere;
Stage #2: With hydrogenchloride In ethanol; water at 120℃; for 8h;
3,4-dihydro-7-methyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1,5-benzodioxepine
944558-64-9

3,4-dihydro-7-methyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1,5-benzodioxepine

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / vanadium pentoxide; aq. H2O2 / acetonitrile / 70 °C
2: 87 percent / aq. KOH; KMnO4 / 2.5 h
View Scheme
4-methyl-1,2-dihydroxybenzene
452-86-8

4-methyl-1,2-dihydroxybenzene

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 83 percent / K2CO3 / dimethylformamide / 0.07 h / microwave irradiation
2.1: tBuOK / tetrahydrofuran / 0.5 h / 70 °C
2.2: 0.59 g / aq. HCl / ethanol / 2 h / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide; ammonium iodide / acetone; ethanol / 4 h / Reflux
2: sulfuric acid / acetone / 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide; potassium iodide / ethanol; water / 4 h / Reflux
2: sulfuric acid / acetone / 6 h / Reflux
View Scheme
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-one oxime

7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-one oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In water; acetonitrile at 50℃; for 24h;94%
With hydroxylamine hydrochloride; sodium acetate In water; acetonitrile at 50℃; for 24h;90%
With hydroxylamine hydrochloride
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

(±)-7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-ol
944558-65-0

(±)-7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 25℃; for 1h; Inert atmosphere;92%
With hydrogen In methanol at 100℃; under 30003 Torr; for 12h; Autoclave;91.2%
With sodium tetrahydroborate In methanol; water at 20℃; for 4h;89%
With sodium tetrahydroborate In ethanol for 1h; Reflux;80%
3-chlorophenyl-isothiocyanate
2392-68-9

3-chlorophenyl-isothiocyanate

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

C20H16ClN3O3S
1258873-71-0

C20H16ClN3O3S

Conditions
ConditionsYield
Stage #1: 3-chlorophenyl-isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
90%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

C20H17N3O3S
1258873-69-6

C20H17N3O3S

Conditions
ConditionsYield
Stage #1: phenyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
89%
4-fluorophenyl isothiocyanate
1544-68-9

4-fluorophenyl isothiocyanate

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

C20H16FN3O3S
1258873-70-9

C20H16FN3O3S

Conditions
ConditionsYield
Stage #1: 4-fluorophenyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
89%
4-Chlorophenyl isothiocyanate
2131-55-7

4-Chlorophenyl isothiocyanate

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

C20H16ClN3O3S
1258873-72-1

C20H16ClN3O3S

Conditions
ConditionsYield
Stage #1: 4-Chlorophenyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
87%
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

7-bromo-8-methyl-2H-1,5-benzodioxepin-3(4H)-one

7-bromo-8-methyl-2H-1,5-benzodioxepin-3(4H)-one

Conditions
ConditionsYield
With sodium bromate; sodium disulfite In cyclohexane; water at 50℃; for 8h;85%
Cyanothioacetamide
7357-70-2

Cyanothioacetamide

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

C20H17N3O2S2
1258873-82-3

C20H17N3O2S2

Conditions
ConditionsYield
Stage #1: Cyanothioacetamide; phenyl isothiocyanate With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
82%
Benzyl isothiocyanate
622-78-6

Benzyl isothiocyanate

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

C21H19N3O3S
1258873-68-5

C21H19N3O3S

Conditions
ConditionsYield
Stage #1: Benzyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
81%
isothiocyanatocyclohexane
1122-82-3

isothiocyanatocyclohexane

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

C20H23N3O3S
1258873-67-4

C20H23N3O3S

Conditions
ConditionsYield
Stage #1: isothiocyanatocyclohexane; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
80%
trimethyl orthoformate
149-73-5

trimethyl orthoformate

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

3,4-dihydro-3,3-dimethoxy-7-methyl-2H-1,5-benzodioxepine

3,4-dihydro-3,3-dimethoxy-7-methyl-2H-1,5-benzodioxepine

Conditions
ConditionsYield
With methanol; trifluorormethanesulfonic acid In nitromethane at 100℃; for 3h;72%
malononitrile
109-77-3

malononitrile

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)malononitrile
1323441-44-6

2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)malononitrile

Conditions
ConditionsYield
With piperidine; acetic acid In benzene Reflux;52%
ethylene glycol
107-21-1

ethylene glycol

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxolane]
1323441-46-8

7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxolane]

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 12h; Reflux;45%
trimethyleneglycol
504-63-2

trimethyleneglycol

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxane]
1323441-47-9

7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxane]

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 12h; Reflux;38%
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

3,4-dihydro-7-methyl-2H-1,5-benzodioxepin-3-yl acetate

3,4-dihydro-7-methyl-2H-1,5-benzodioxepin-3-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / NaBH4 / H2O; methanol / 4 h / 20 °C
2: 88 percent / Et3N / diethyl ether / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / diethyl ether / 1 h / 25 °C / Inert atmosphere
2: pyridine / 2 h / 100 °C / Inert atmosphere
View Scheme
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

3,4-dihydro-7-methyl-2H-1,5-benzodioxepin-3-yl benzoate

3,4-dihydro-7-methyl-2H-1,5-benzodioxepin-3-yl benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / NaBH4 / H2O; methanol / 4 h / 20 °C
2: 44 percent / Et3N / diethyl ether / 2 h / 20 °C
View Scheme
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

3,4-dihydro-7-methyl-2H-1,5-benzodioxepin-3-yl prop-2-enoate

3,4-dihydro-7-methyl-2H-1,5-benzodioxepin-3-yl prop-2-enoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / NaBH4 / H2O; methanol / 4 h / 20 °C
2: 22 percent / Et3N / diethyl ether / 2 h / 20 °C
View Scheme
7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

7-methyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-3-amine

7-methyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / hydroxylamine hydrochloride; AcONa / acetonitrile; H2O / 24 h / 50 °C
2: 54 percent / NaBH4; TiCl4 / 1,2-dimethoxy-ethane / 24 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium acetate / water; acetonitrile / 24 h / 50 °C
2: sodium tetrahydroborate; titanium tetrachloride / diethyl ether / 24 h / 20 °C / Inert atmosphere
View Scheme
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

A

cis-ethyl-2-cyano-2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)acetate
1323441-45-7

cis-ethyl-2-cyano-2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)acetate

B

trans-ethyl-2-cyano-2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)acetate

trans-ethyl-2-cyano-2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)acetate

Conditions
ConditionsYield
With piperidine; acetic acid In benzene Reflux;
4-(N,N-dibutylamino)benzaldehyde
90134-10-4

4-(N,N-dibutylamino)benzaldehyde

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

7-methyl-2,4-bis[1-(4-dibutylaminophenyl)meth-(Z)-ylidene]benzo[b]-1,4-dioxepin-3-one
1430403-92-1

7-methyl-2,4-bis[1-(4-dibutylaminophenyl)meth-(Z)-ylidene]benzo[b]-1,4-dioxepin-3-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 50℃; for 40h;1.45 g
asaraldehyde
4460-86-0

asaraldehyde

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

7-methyl-2,4-bis[1-(2,4,5-trimethoxyphenyl)meth-(Z)-ylidene]benzo[b]-1,4-dioxepin-3-one
1430403-79-4

7-methyl-2,4-bis[1-(2,4,5-trimethoxyphenyl)meth-(Z)-ylidene]benzo[b]-1,4-dioxepin-3-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 40℃; for 2h;1.45 g

28940-11-6Relevant articles and documents

KI-catalysed synthesis of 4-methylcatechol dimethylacetate and fragrant compound Calone 1951

Zhang, Ya-Zheng,Yang, Qian,Huang, Shao-Jian,Luo, Zi-Ping,Li, Wen-Ping,Dong, Li-Chun

, p. 586 - 593 (2013)

Synthesis of the fragrant compound Calone 1951 from 4-methyl catechol and methyl bromoacetate entails three successive reactions: the Williamson reaction, Dieckmann condensation, and hydrolysis-decarboxylation reaction. In this paper, the synthesis of 4-methylcatechol dimethylacetate (MCDA) via the Williamson reaction by adding KI as catalyst was investigated. It was found that the addition of an appropriate amount of KI can significantly increase the product yield due to generation of methyl iodoacetate via the reaction between KI and methyl bromoacetate. The synthesised MCDA as well as Calone 1951 were first characterised by melting points, HPLC, IR, and NMR analyses. Next, the effect of the key operating factors on MCDA synthesis by the Williamson reaction was investigated and the optimum operating conditions were obtained via a group of orthogonal experiments. The verification experiments demonstrated that, under the optimum operating conditions, the MCDA yield could be increased from 78.5 % to 95.4 % by the addition of an appropriate amount of KI; the corresponding yield of Calone 1951 increased to 68 %.

Method for synthesizing watermelon ketone

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Paragraph 0034-0059, (2021/11/19)

The invention belongs to the technical field of perfume compound synthesis. The invention specifically relates to a synthesis method of watermelon ketone. The method comprises the following steps: adding a solvent and a periodate into the reaction vessel at room temperature, stirring uniformly, and then dropwise adding the watermelon ketone precursor alcohol (I) dissolved by the solvent to the reaction vessel to obtain a crude watermelon ketone crude product which is subjected to recrystallization to obtain the watermelon ketone (3 - 7h II) finished product. To the invention, 4 - methylcatechol and 1, 3 -dichloropropanol reaction product 3, 4 - dihydro -7 - methyl - 2H - 1 and 5 - benzoxazole -3 - alcohol (I) are used as starting materials and are subjected to high-iodine reagent oxidation reaction. High yields were obtained. The high-purity citrulline (II) has the advantages of simple process, high product yield, high purity and low cost, and is suitable for industrial production.

A Deoximation Method for Deprotection of Ketones and Aldhydes Using a Graphene-Oxide-Based Co-catalysts System

Tong, Qiaolin,Liu, Yang,Gao, Xuezhi,Fan, Zhanfang,Liu, Tianfu,Li, Bo,Su, Dangsheng,Wang, Qinghe,Cheng, Maosheng

supporting information, p. 3137 - 3145 (2019/05/01)

The deoximation of a wide range of ketoximes and aldoximes to their corresponding carbonyl compounds with high yields has been achieved using graphene oxide (GO) and sodium nitrite (NaNO2) as highly efficient catalysts and air as the green oxidant under mild conditions. The mechanism of deprotection and recycling use of catalyst were revealed in deep experiment. The carboxylic acid groups on the GO were essential for high catalytic activity. (Figure presented.).

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