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60047-17-8

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60047-17-8 Usage

General Description

Linalool oxide is a monoterpenoid compound, commonly found in some species of the aromatic plants. It can be obtained from linalool either by oxidation or via biotransfomation using the fungus Aspergillus niger. It is always present as a mixture of both cis and trans forms.

Check Digit Verification of cas no

The CAS Registry Mumber 60047-17-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,0,0,4 and 7 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 60047-17:
(7*6)+(6*0)+(5*0)+(4*4)+(3*7)+(2*1)+(1*7)=88
88 % 10 = 8
So 60047-17-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3

60047-17-8 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (L0143)  Linalool Oxide (mixture of isomers)  >97.0%(GC)

  • 60047-17-8

  • 25mL

  • 520.00CNY

  • Detail
  • Aldrich

  • (62141)  Linalooloxide  mixture of isomers, ≥97.0% (GC)

  • 60047-17-8

  • 62141-25ML

  • 600.21CNY

  • Detail

60047-17-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(2-Hydroxy-2-Propyl)-5-Methyl-5-Vinyltetrahydrofuran

1.2 Other means of identification

Product number -
Other names Linalool oxide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:60047-17-8 SDS

60047-17-8Synthetic route

1-(5-ethynyl-5-methyl-2-tetrahydrofuranyl)-1-methylethanol
97277-67-3

1-(5-ethynyl-5-methyl-2-tetrahydrofuranyl)-1-methylethanol

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
With quinoline; hydrogen; Pd-BaSO4 In methanol Ambient temperature;92%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

A

6,7-epoxylinalool
15249-35-1

6,7-epoxylinalool

B

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
With pyridine; pyridine-3-carbonitrile; dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at -0.15℃; for 1.7h; Yields of byproduct given;A 82%
B n/a
5,6-epoxy-6-methyl-2-heptanone
16262-93-4

5,6-epoxy-6-methyl-2-heptanone

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
In tetrahydrofuran for 12h; Ambient temperature;75%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
With maleic anhydride; urea-hydrogen peroxide complex In dichloromethane at 0℃; for 5h;75%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0℃; for 8h;72%
With Beauveria sulfurescens ATCC7159 In various solvent(s) for 16h;
C17H26O5S

C17H26O5S

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
With potassium tert-butylate; tert-butyl alcohol at 70 - 80℃; for 6h;72.91%
2-[5-(1-Iodo-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol

2-[5-(1-Iodo-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 25℃;70%
(2E)-3-methyl-5-{(4R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl}-2-pentene-1-ol
119906-63-7

(2E)-3-methyl-5-{(4R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl}-2-pentene-1-ol

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

A

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

B

C14H23F3O5S

C14H23F3O5S

Conditions
ConditionsYield
at -78℃;A n/a
B 43%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

(4'S,2E)-3-methyl-5-(2',2',5',5'-tetramethyl-1',3'-dioxolan-4'-yl)-2-penten-1-ol
61262-97-3

(4'S,2E)-3-methyl-5-(2',2',5',5'-tetramethyl-1',3'-dioxolan-4'-yl)-2-penten-1-ol

A

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

B

C14H23F3O5S

C14H23F3O5S

Conditions
ConditionsYield
at -78℃;A n/a
B 43%
peracetic acid
79-21-0

peracetic acid

linalool
126-91-0

linalool

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

monoperoxyphthalic acid
2311-91-3

monoperoxyphthalic acid

linalool
126-91-0

linalool

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Acetic acid 1-[5-(1-iodo-ethyl)-5-methyl-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

Acetic acid 1-[5-(1-iodo-ethyl)-5-methyl-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
With potassium tert-butylate; hydroxide 1) DMF, 25 deg C; Yield given. Multistep reaction;
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

A

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

B

3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran
14049-11-7

3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran

Conditions
ConditionsYield
With cetylpyridinium peroxotungstophosphate; dihydrogen peroxide In chloroform; water for 1h; Ambient temperature;A 48 % Chromat.
B 22 % Chromat.
With tert.-butylhydroperoxide; Ti-MCM-41 zeolite In acetonitrile at 79.9℃; for 24h; Product distribution; var. of catalyst, time;A 37.8 % Turnov.
B 42.3 % Turnov.
With cetylpyridinium peroxotungstophosphate; dihydrogen peroxide In chloroform; water for 1h; Mechanism; Ambient temperature;A 48 % Chromat.
B 22 % Chromat.
oct-1-ene
111-66-0

oct-1-ene

A

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

B

1,2-Epoxyoctane
2984-50-1

1,2-Epoxyoctane

Conditions
ConditionsYield
With cetylpyridinium peroxotungstophosphate; dihydrogen peroxide In chloroform; tert-butyl alcohol at 60℃; for 8h;A 48 % Chromat.
B 76 % Chromat.
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

A

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

B

3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran
14049-11-7

3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran

C

Nerol
106-25-2

Nerol

Conditions
ConditionsYield
With titanium silicate; dihydrogen peroxide In methanol; water at 59.84℃; for 24h;
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

A

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

B

Nerol
106-25-2

Nerol

Conditions
ConditionsYield
With dihydrogen peroxide; aluminium In methanol; water at 59.84℃; for 31h;
3,7-dimethyloct-6-en-1-yn-3-ol
29171-20-8

3,7-dimethyloct-6-en-1-yn-3-ol

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaBr / acetonitrile; H2O / 9 h / Ambient temperature; electrolysis
2: NaOH / acetonitrile; H2O / 1 h / Ambient temperature
3: 92 percent / H2(g), quinoline / 5percent Pd/BaSO4 / methanol / Ambient temperature
View Scheme
5-(3,3-Dimethyl-oxiranyl)-3-methyl-pent-1-yn-3-ol
74026-67-8

5-(3,3-Dimethyl-oxiranyl)-3-methyl-pent-1-yn-3-ol

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / acetonitrile; H2O / 1 h / Ambient temperature
2: 92 percent / H2(g), quinoline / 5percent Pd/BaSO4 / methanol / Ambient temperature
View Scheme
2,3-Dihydroxy-2,6-dimethyl-octen-(6)
78631-57-9

2,3-Dihydroxy-2,6-dimethyl-octen-(6)

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: I2, NaHCO3 / acetonitrile / 0 °C
2: 70 percent / KO-t-Bu / dimethylformamide / 25 °C
View Scheme
Acetic acid (E)-2-benzyloxy-1,1,5-trimethyl-hept-5-enyl ester
78631-58-0

Acetic acid (E)-2-benzyloxy-1,1,5-trimethyl-hept-5-enyl ester

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: I2 / acetonitrile / 0 °C
2: 1.) KO-t-Bu, 2.) OH(1-) / 1) DMF, 25 deg C
View Scheme
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

A

6,7-epoxylinalool
15249-35-1

6,7-epoxylinalool

B

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

C

3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran
14049-11-7

3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran

Conditions
ConditionsYield
With [(n-C6H13)4N]3[PO4[WO(O2)2]4]; dihydrogen peroxide In water; acetonitrile at 80℃; for 5h; Catalytic behavior;
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

A

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

B

3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran
14049-11-7

3-hydroxy-2,2,6-trimethyl-6-vinyltetrahydropyran

C

epoxy-linalooloxide
861071-75-2

epoxy-linalooloxide

Conditions
ConditionsYield
With 4C19H34N(1+)*HBW4O24(4-); dihydrogen peroxide In water; acetonitrile at 80℃; for 5h; Catalytic behavior;
With 7C16H36N(1+)*3H(1+)*2H2O*(Co2PW9O34)2(10-); dihydrogen peroxide In water; acetonitrile at 80℃; for 5h; Catalytic behavior; Reagent/catalyst; Temperature;
Essigsaeure-<(6S,2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl>ester
61302-43-0

Essigsaeure-<(6S,2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl>ester

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C
2: potassium carbonate / methanol / 24 h / 20 °C
3: -78 °C
View Scheme
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C
2: potassium carbonate / methanol / 24 h / 20 °C
3: -78 °C
4: Irradiation
View Scheme
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C
2: potassium carbonate / methanol / 24 h / 20 °C
3: phosphorus tribromide / diethyl ether / 0.33 h / -7 °C
4: Irradiation
View Scheme
Essigsaeure-<(6S,2E)-6,7-isopropylidendioxy-3,7-dimethyl-2-octen-1-yl>ester
61262-98-4

Essigsaeure-<(6S,2E)-6,7-isopropylidendioxy-3,7-dimethyl-2-octen-1-yl>ester

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / methanol / 24 h / 20 °C
2: -78 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / methanol / 24 h / 20 °C
2: -78 °C
3: Irradiation
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / methanol / 24 h / 20 °C
2: phosphorus tribromide / diethyl ether / 0.33 h / -7 °C
3: Irradiation
View Scheme
(2E)-3-methyl-5-{(4R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl}-2-pentene-1-ol
119906-63-7

(2E)-3-methyl-5-{(4R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl}-2-pentene-1-ol

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphorus tribromide / diethyl ether / 0.33 h / -7 °C
2: Irradiation
View Scheme
Multi-step reaction with 2 steps
1: -78 °C
2: Irradiation
View Scheme
(4'S,2E)-3-methyl-5-(2',2',5',5'-tetramethyl-1',3'-dioxolan-4'-yl)-2-penten-1-ol
61262-97-3

(4'S,2E)-3-methyl-5-(2',2',5',5'-tetramethyl-1',3'-dioxolan-4'-yl)-2-penten-1-ol

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphorus tribromide / diethyl ether / 0.33 h / -7 °C
2: Irradiation
View Scheme
Multi-step reaction with 2 steps
1: -78 °C
2: Irradiation
View Scheme
(4'S,2E)-1-brom-3-methyl-5-(2',2',5',5'-tetramethyl-1',3'-dioxolan-4'-yl)-2-penten
116660-94-7

(4'S,2E)-1-brom-3-methyl-5-(2',2',5',5'-tetramethyl-1',3'-dioxolan-4'-yl)-2-penten

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Irradiation;
C14H23F3O5S

C14H23F3O5S

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Irradiation;
C14H23F3O5S

C14H23F3O5S

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Irradiation;
essigsaeure-<(E,R)-6,7-dihydroxy-3,7-dimethyl-2-octenyl>ester
86561-84-4

essigsaeure-<(E,R)-6,7-dihydroxy-3,7-dimethyl-2-octenyl>ester

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C
2: potassium carbonate / methanol / 24 h / 20 °C
3: -78 °C
View Scheme
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C
2: potassium carbonate / methanol / 24 h / 20 °C
3: -78 °C
4: Irradiation
View Scheme
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C
2: potassium carbonate / methanol / 24 h / 20 °C
3: phosphorus tribromide / diethyl ether / 0.33 h / -7 °C
4: Irradiation
View Scheme
2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

methyl-2 ethyl-2 (methyl-1 hydroxy-1 ethyl)-5 tetrahydrofuranne

methyl-2 ethyl-2 (methyl-1 hydroxy-1 ethyl)-5 tetrahydrofuranne

Conditions
ConditionsYield
With triethylsilane; 1% Pd on activated carbon In water at 20℃; for 12h; Reagent/catalyst; Green chemistry; chemoselective reaction;99%
With hydrogen; palladium 10% on activated carbon In methanol at 30℃;88%
2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

5-methyl-5-vinyl-dihydro-furan-2-one
1073-11-6

5-methyl-5-vinyl-dihydro-furan-2-one

Conditions
ConditionsYield
With 3 A molecular sieve; pyridinium chlorochromate In dichloromethane for 3h; Heating;73%
With 3 A molecular sieve; pyridinium chlorochromate In dichloromethane for 4h; Heating;73%
2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

acetyl chloride
75-36-5

acetyl chloride

acetic acid 1-methyl-1-(5-methyl-5-vinyl-tetrahydro-furan-2-yl)-ethyl ester

acetic acid 1-methyl-1-(5-methyl-5-vinyl-tetrahydro-furan-2-yl)-ethyl ester

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0 - 20℃; Acetylation;53%
2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

ethyl vinyl ether
109-92-2

ethyl vinyl ether

5-(2-(1-ethoxyethoxy)propan-2-yl)-2-methyl-2-vinyltetrahydrofuran

5-(2-(1-ethoxyethoxy)propan-2-yl)-2-methyl-2-vinyltetrahydrofuran

Conditions
ConditionsYield
With toluene-4-sulfonic acid In diethyl ether at 5 - 20℃; for 12.5h;37%
monomethyl oxalyl chloride
5781-53-3

monomethyl oxalyl chloride

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

C13H20O5

C13H20O5

C13H20O5

C13H20O5

Conditions
ConditionsYield
With pyridine In diethyl ether at 22℃; for 16h; Inert atmosphere;A 30%
B 32%
2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

2,6-dimethyl-octa-4,6-dien-3-one
91056-18-7

2,6-dimethyl-octa-4,6-dien-3-one

Conditions
ConditionsYield
With hydrogen cation
carbon disulfide
75-15-0

carbon disulfide

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

C11H17O2S2(1-)*Na(1+)

C11H17O2S2(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydride 1.) THF, RT, 1 h, 2.) THF, 20 min; Multistep reaction;
2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

A

2,2,5-trimethylcyclohept-4-en-1-one
19822-67-4

2,2,5-trimethylcyclohept-4-en-1-one

B

(4E,6E)-2,6-Dimethyl-octa-4,6-dien-3-one
91056-18-7

(4E,6E)-2,6-Dimethyl-octa-4,6-dien-3-one

Conditions
ConditionsYield
With potassium hydrogensulfate at 200℃; for 0.5h;A 0.7 % Chromat.
B 41 % Chromat.
carbon disulfide
75-15-0

carbon disulfide

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

xanthate of 1-(5-ethenyl-5-methyl-2-tetrahydrofuranyl)-1-methylethanol
97277-68-4

xanthate of 1-(5-ethenyl-5-methyl-2-tetrahydrofuranyl)-1-methylethanol

Conditions
ConditionsYield
With sodium hydride 1.) THF; Multistep reaction;
2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

2,2,5-trimethylcyclohept-4-en-1-one
19822-67-4

2,2,5-trimethylcyclohept-4-en-1-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, 20 min
2: tetrahydrofuran / 0.33 h
3: 200 °C
View Scheme
Multi-step reaction with 4 steps
1: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, 20 min
2: tetrahydrofuran / 0.33 h
3: 200 °C
4: 44 percent / RhCl3*3H2O, Na2CO3 / 10 h / 200 °C
View Scheme
2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

2-methyl-5-(prop-1-en-2-yl)-2-vinyltetrahydrofuran
13679-86-2

2-methyl-5-(prop-1-en-2-yl)-2-vinyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, 20 min
2: tetrahydrofuran / 0.33 h
3: 200 °C
View Scheme
2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran
60047-17-8

2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran

xanthate of 1-(5-ethenyl-5-methyl-2-tetrahydrofuranyl)-1-methylethanol
97277-68-4

xanthate of 1-(5-ethenyl-5-methyl-2-tetrahydrofuranyl)-1-methylethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, 20 min
2: tetrahydrofuran / 0.33 h
View Scheme

60047-17-8Relevant articles and documents

One-pot synthesis at room temperature of epoxides and linalool derivative pyrans in monolacunary Na7PW11O39-catalyzed oxidation reactions by hydrogen peroxide

Da Silva, Márcio J.,Teixeira, Milena Galdino,Vilanculo, Castelo B.,Villarreal, Jesus Avendano

, p. 7691 - 7697 (2020/03/10)

In this work, we describe a new one-pot synthesis route of valuable linalool oxidation derivatives (i.e., 2-(5-methyl-5-vinyltetrahydrofuran-2-yl propan-2-ol) (1a)), 2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol (1b) and diepoxide (1c), using a green oxidant (i.e., hydrogen peroxide) under mild conditions (i.e., room temperature). Lacunar Keggin heteropolyacid salts were the catalysts investigated in this reaction. Among them, Na7PW11O39 was the most active and selective toward oxidation products. All the catalysts were characterized by FT-IR, TG/DSC, BET, XRD analyses and potentiometric titration. The main reaction parameters were assessed. Special attention was dedicated to correlating the composition and properties of the catalysts and their activity.

Asymmetric synthesis and structure-activity studies of the fungal metabolites colletorin A, colletochlorin A and their halogenates analogues

Marsico, Giulia,Pignataro, Barbara A.,Masi, Marco,Evidente, Antonio,Casella, Francesca,Zonno, Maria Chiara,Tak, Jun-Hyung,Bloomquist, Jeffrey R.,Superchi, Stefano,Scafato, Patrizia

, p. 3912 - 3923 (2018/06/08)

The first asymmetric total synthesis of both enantiomers of the natural products colletorin A and colletochlorin A is presented. The proposed methodology is based on the coupling reaction between highly substituted aromatic Gilman cuprates and optically active allyl bromides, in turn obtained by Sharpless asymmetric dihydroxylation. The latter ensured a high degree of regio- and stereocontrol in the enantioselective step of the synthesis. The same synthetic strategy has been also applied for the preparation of differently halogenated synthetic analogues of colletochlorin A in high enantiomeric purity. The enantioselective synthesis of colletorin A and colletochlorin A allows to reliably assign their absolute configuration. Preliminary assessment of their herbicidal and insecticidal properties evidence the possibility to modulate the bioactivity of these compounds, highlighting its dependence on both the absolute stereochemistry and the halogen nature.

Method for preparing furan-type oxidized linalool

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Paragraph 0030-0057, (2017/09/13)

The invention discloses a method for preparing furan-type oxidized linalool. The method specifically comprises the following steps: firstly, at the room temperature, mixing and stirring 4H-5-(1-hydroxyl-1-methyl ethyl)-2-methyl-2-furan ethanol, paratoluensulfonyl chloride and alkali to implement reaction, after the reaction is completed, adjusting the pH value to be neutral by using an acid solution, extracting, drying and filtering; performing evaporation concentration on the filtrate so as to obtain sulfonate; adding potassium tert-butoxide and tertiary butanol into the sulfonate, and performing reaction at 70-80 DEG C so as to obtain a crude product; and performing purification treatment on the crude product, thereby obtaining the furan-type oxidized linalool. The method disclosed by the invention is easy in raw material obtaining, simple in preparation process, convenient to operate, relatively low in production cost and applicable to industrial production.

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