62285-98-7

Basic information

• Product Name: [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide
• Synonyms: [5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienyl];[5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadienyl]triphenylphosphonium bromide;[3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl]triphenylphosphonium bromide;((2E,4E)-3-Methyl-5-(2,6,6-triMethylcyclohex-1-en-1-yl)penta-2,4-dien-1-yl)triphenylphosphoniuM broMide;((2E,4E)-3-Methyl-5-(2,6,6-trimethylcyclohex-2-en-1-yl)penta-2,4-dien-1-yl)triphenylphosphonium bromide;[(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide
• CAS NO: 62285-98-7
• Molecular Formula: Br*C₃₃H₃₈P
• Molecular Weight: 545.53
• EINECS: 1312995-182-4
• Mol File: 62285-98-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide(62285-98-7)
• EPA Substance Registry System: [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadien-1-yl](triphenyl)phosphonium bromide(62285-98-7)

Safety Data

• Hazardous Substances Data: 62285-98-7(Hazardous Substances Data)

Usage

Uses

[(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadien-1-yl]triphenyl-phosphonium Bromide is used in the synthesis of all-trans-retinoic acid (ATRA), a precursor of vitamin A

InChI:InChI=1S/C33H38P.BrH/c1-27(22-23-32-28(2)15-14-25-33(32,3)4)24-26-34(29-16-8-5-9-17-29,30-18-10-6-11-19-30)31-20-12-7-13-21-31;/h5-13,15-24,32H,14,25-26H2,1-4H3;1H/q+1;/p-1/b23-22+,27-24+;

Synthetic route

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol (59057-30-6) + triphenylphosphine hydrobromide (6399-81-1) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
In methanol for 75h; Ambient temperature;	100%
In methanol at 20℃; for 20h;	73%
In tetrahydrofuran

3-methyl-5-bromo-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene (38987-92-7) + triphenylphosphine (603-35-0) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
In acetonitrile at 50 - 55℃; for 5h; Inert atmosphere;	92.8%
In acetonitrile at 50 - 55℃; for 5h; Inert atmosphere;	92.1%

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol (3917-39-3) + triphenylphosphine hydrobromide (6399-81-1) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
In methanol for 17h; Ambient temperature;

triphenylphosphine hydrobromide (6399-81-1) + Acetic acid (2Z,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl ester → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + β-ionylidenetriphenylphosphonium bromide

Conditions	Yield
Stage #1: Acetic acid (2Z,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl ester With lithium aluminium tetrahydride Stage #2: triphenylphosphine hydrobromide

(E)-β-ionone (79-77-6) + vinyl magnesium bromide (1826-67-1) + triphenylphosphine hydrobromide (6399-81-1) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Stage #1: (E)-β-ionone; vinyl magnesium bromide Stage #2: triphenylphosphine hydrobromide Further stages.;

(E)-β-ionone (79-77-6) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / tetrahydrofuran / 20 h / 20 °C 2: 73 percent / methanol / 20 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 94 percent / tetrahydrofuran / 14 h / Ambient temperature 2: 100 percent / methanol / 75 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 24 h / 20 °C 2.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C 2.2: 24 h / 20 °C View Scheme

(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate (17974-55-9) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether / 0.25 h / Ambient temperature 2: methanol / 17 h / Ambient temperature View Scheme

[5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2-penten-4-ynyl]triphenylphosphonium bromide + 2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol (5244-34-8) + nickel (7440-02-0) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
In methanol; dichloromethane; ethyl acetate

(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate (17974-55-9) + triphenylphosphine hydrobromide (6399-81-1) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Stage #1: (2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.5h; Stage #2: triphenylphosphine hydrobromide In methanol at 20℃; for 24h;

2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene (59633-88-4) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hexane / 4 h / 50 - 55 °C / Inert atmosphere 2.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere 3.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C 3.2: 3 h / 20 - 25 °C 4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

C28H32P(1+)*Cl(1-) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere 2.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C 2.2: 3 h / 20 - 25 °C 3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

diethyl [(2,2,6-trimethylcyclohexyl)methyl]phosphonate → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium methylate / N,N-dimethyl-formamide / 1 h / 0 - 15 °C / Inert atmosphere 2.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C 2.2: 3 h / 20 - 25 °C 3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide (56013-01-5) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere 2.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C 2.2: 3 h / 20 - 25 °C 3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

3-methyl-5-acetoxy-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene (3917-38-2) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C 1.2: 3 h / 20 - 25 °C 2.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

3,7-dimethylocta-1,6-dien-3-ol (78-70-6) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogen bromide; sodium hydroxide / water; dichloromethane / 2 h / 30 - 35 °C / Inert atmosphere 1.2: 2 h / 35 - 40 °C 2.1: hexane / 4 h / 50 - 55 °C / Inert atmosphere 3.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere 4.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C 4.2: 3 h / 20 - 25 °C 5.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: sodium hydroxide; thionyl chloride / 1,2-dichloro-ethane; water / 3 h / 40 - 45 °C 1.2: 5 h / 70 - 75 °C 2.1: acetonitrile / 4 h / 60 - 65 °C / Inert atmosphere 3.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere 4.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C 4.2: 3 h / 20 - 25 °C 5.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: sodium hydroxide; thionyl chloride / 1,2-dichloro-ethane; water / 3 h / 40 - 45 °C 1.2: 5 h / 70 - 75 °C 2.1: 4 h / 105 - 110 °C / Inert atmosphere 3.1: sodium methylate / N,N-dimethyl-formamide / 1 h / 0 - 15 °C / Inert atmosphere 4.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C 4.2: 3 h / 20 - 25 °C 5.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

1,3,3-trimethyl-2-chloromethylcyclohexene → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetonitrile / 4 h / 60 - 65 °C / Inert atmosphere 2.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere 3.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C 3.2: 3 h / 20 - 25 °C 4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: 4 h / 105 - 110 °C / Inert atmosphere 2.1: sodium methylate / N,N-dimethyl-formamide / 1 h / 0 - 15 °C / Inert atmosphere 3.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C 3.2: 3 h / 20 - 25 °C 4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

4-bromo-3-methyl-2-buten-1-ol acetate (32659-14-6) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetonitrile / 4 h / 60 - 65 °C / Inert atmosphere 2.1: sodium ethanolate / N,N-dimethyl-formamide / 2 h / 0 - 5 °C / Inert atmosphere 3.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C 3.2: 3 h / 20 - 25 °C 4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: methanol / 4 h / 100 - 105 °C / Inert atmosphere 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / -10 - 0 °C / Inert atmosphere 3.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C 3.2: 3 h / 20 - 25 °C 4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: ethanol / 4 h / 105 - 110 °C / Inert atmosphere 2.1: sodium ethanolate / toluene / 2 h / -5 - 5 °C / Inert atmosphere 3.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C 3.2: 3 h / 20 - 25 °C 4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

C25H26O2P(1+)*Br(1-) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium ethanolate / N,N-dimethyl-formamide / 2 h / 0 - 5 °C / Inert atmosphere 2.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C 2.2: 3 h / 20 - 25 °C 3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

C25H26O2P(1+)*Cl(1-) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium methylate / N,N-dimethyl-formamide / 2 h / 5 - 10 °C / Inert atmosphere 2.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C 2.2: 3 h / 20 - 25 °C 3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

diethyl 2-methyl-4-acetoxy-2-butenylphosphonate → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium ethanolate / toluene / 2 h / -5 - 5 °C / Inert atmosphere 2.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C 2.2: 3 h / 20 - 25 °C 3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

dimethyl 2-methyl-4-acetoxy-2-butenylphosphonate → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / -10 - 0 °C / Inert atmosphere 2.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C 2.2: 3 h / 20 - 25 °C 3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

(E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol (24529-80-4) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetonitrile / 4 h / 70 - 75 °C / Inert atmosphere 2.1: sodium methylate / N,N-dimethyl-formamide / 2 h / 5 - 10 °C / Inert atmosphere 3.1: sodium hydroxide / dichloromethane; water / 3 h / 15 - 20 °C 3.2: 3 h / 20 - 25 °C 4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere View Scheme

4-palmitoyloxy-2-methyl-2-buten-1-al + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → retinyl palmitate (79-81-2)

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at -5 - 5℃; for 3h; Wittig Olefination; Inert atmosphere;	91.3%

(E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → Retinol acetate (127-47-9)

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at -5 - 0℃; for 2h; Solvent; Temperature; Reagent/catalyst; Wittig Olefination; Inert atmosphere;	91%
With sodium ethanolate In N,N-dimethyl-formamide at -5 - 5℃; for 2h; Time; Inert atmosphere;	90.7%

(Z)-3-methyl-4-oxobut-2-enoic acid (70143-04-3) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → 13-cis-retinoic acid (4759-48-2)

Conditions	Yield
Stage #1: (Z)-3-methyl-4-oxobut-2-enoic acid; 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide With sodium hydroxide In isopropyl alcohol at 20 - 30℃; for 3h; Wittig Olefination; Inert atmosphere; Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 60℃; pH=7 - 8;	86.3%
Stage #1: (Z)-3-methyl-4-oxobut-2-enoic acid; 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide With sodium hydroxide In isopropyl alcohol at 20 - 30℃; for 3h; Wittig Olefination; Inert atmosphere; Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 60℃; pH=7-8; Inert atmosphere;	86.3%

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + 4-formyl-2-[3-oxo-2-methyl-(1E)-propenyl]pyridine (188554-16-7) → 2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridine (188554-17-8)

Conditions	Yield
With sodium ethanolate In ethanol	76%

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + (Z)-3-Iodo-4-oxo-but-2-enoic acid ethyl ester (174836-86-3) → (2Z,4E,6E,8E)-3-Iodo-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid ethyl ester (743421-41-2)

Conditions	Yield
Stage #1: (Z)-3-Iodo-4-oxo-but-2-enoic acid ethyl ester With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide Stage #2: 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide Further stages.;	74%

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + bis(3-formyl-3-methyl-2-propenyl) sulfide (251291-80-2) → retinyl sulfide (268728-47-8)

Conditions	Yield
Stage #1: 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide; bis(3-formyl-3-methyl-2-propenyl) sulfide In DMF (N,N-dimethyl-formamide) at -20℃; Stage #2: With sodium methylate In DMF (N,N-dimethyl-formamide) at -20 - 20℃; for 3.5h;	68%

4-t-butyldimethylsilyloxy-2-butynal (75859-97-1) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → tert-Butyl-dimethyl-[(4Z,6E,8E)-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trien-2-ynyloxy]-silane (75867-37-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran for 3h; Ambient temperature;	52%

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + 2-methyl-3-[3-(1-methyl-2-oxoethylidene)-cyclohex-1-enyl]-propenal (454442-05-8) → C43H60

Conditions	Yield
With sodium methylate In methanol for 1h;	40%

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + 13-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethylcyclohex-1-enyl]-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal → (all-E)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene (135589-15-0) + (9'Z)-(3R)-3-(β-D-glucopyranosyloxy)-β,β-carotene

Conditions	Yield
Stage #1: 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide; 13-[(4R)-4-(β-D-glucopyranosyloxy)-2,6,6-trimethylcyclohex-1-enyl]-2,7,11-trimethyltrideca-2,4,6,8,10,12-hexaenal With sodium methylate In methanol; dichloromethane at 20℃; for 3h; Wittig condensation; Stage #2: With Dowex 50W-X8 (H+) In methanol; dichloromethane at 20℃; for 0.333333h;	A 28% B 10%

(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal (103956-99-6, 1071-52-9) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → trans-gamma-Carotene (472-93-5)

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide

2-Methyl-4-(thioacetyl)-2-(E)-butenal (72053-20-4) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → 11-cis-Retinylthioacetat (72053-19-1, 72075-18-4)

Conditions	Yield
(i) nBuLi, (ii) /BRN= 2075468/; Multistep reaction;

2-Methyl-4-(thioacetyl)-2-(E)-butenal (72053-20-4) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → 11-trans-Retinylthioacetat (72053-19-1, 72075-18-4)

Conditions	Yield
(i) nBuLi, (ii) /BRN= 2075468/; Multistep reaction;

acetic acid trans-4-oxo-but-2-enyl ester (38982-39-7) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → Acetic acid (2E,4E,6E,8E)-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyl ester

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane 1.) 1 h, -60 deg C; 2.) 2 h to RT; Yield given;

ethyl-2-formyl-1-cyclopropane carboxylate (13949-93-4, 13950-12-4, 77183-91-6, 77183-92-7, 109716-50-9, 109716-61-2, 20417-61-2) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → ethyl trans-13,14-dihydro-13-desmethyl-13,14-methyleneretinoate (89887-40-1) + ethyl cis-13,14-dihydro-13-desmethyl-13,14-methyleneretinoate (89827-99-6)

Conditions	Yield
With potassium tert-butylate benzene, 1) 15 min 2) 8h, r.t.; Yield given. Multistep reaction. Yields of byproduct given;

1-Carbethoxy-2-formyl-2-methyl-cyclopropan (20417-63-4) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → ethyl trans-13,14-dihydro-13,14-methyleneretinoate (89887-37-6) + ethyl cis-13,14-dihydro-13,14-methyleneretinoate (89827-98-5)

Conditions	Yield
With potassium tert-butylate benzene, 1) 15 min 2) 22h, r.t.; Yield given. Multistep reaction. Yields of byproduct given;

4,4-dimethoxy-3-methyl-but-2-en-1-al (62285-97-6) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → 2-((1E,3E,5E,7E)-9,9-Dimethoxy-3,8-dimethyl-nona-1,3,5,7-tetraenyl)-1,3,3-trimethyl-cyclohexene

Conditions	Yield
With sodium ethanolate In ethanol; dichloromethane at 0℃; for 1h;

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + 4-(tert-butyldimethylsilyloxy)-2-methylbutanal (115797-15-4) → 13,14-dihydro-all-trans retinol (115797-14-3)

Conditions	Yield
With tetrabutyl ammonium fluoride 1.) Wittig-reaction; Multistep reaction;

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienylidenetriphenylphosphorane (71987-74-1)

Conditions	Yield
With phenyllithium In diethyl ether for 0.0833333h; Ambient temperature;

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + (2E,4E,6E,8E,10E)-2,7,11-trimethyl-12-oxotrideca-2,4,6,8,10-pentaenal (160456-53-1) → (all-E)-sintaxanthin (4586-97-4)

Conditions	Yield
With sodium hydride In dichloromethane at 20℃; for 48h; Yield given;

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → 12'-apo-β-caroten-12'-al (1638-05-7)

Conditions	Yield
With sodium hydride In dichloromethane at 20℃; for 64h; Yield given;
With sodium methylate In methanol at 0℃; for 0.5h; Wittig olefination;

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + 4-formyl-2-[3-oxo-2-methyl-(1E)-propenyl]pyridine (188554-16-7) → 2-[(1E,3Z,5E,7E)-2,4-Dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-1,3,5,7-tetraenyl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-pyridine + 2-[(1E,3Z,5E,7E)-2,6-Dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-1,3,5,7-tetraenyl]-4-[(1Z,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-pyridine + 2-[(1E,3E,5E,7E)-2,6-Dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-1,3,5,7-tetraenyl]-4-[(1Z,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-pyridine + 2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridine (188554-17-8)

Conditions	Yield
With sodium ethanolate 1.) EtOH, room temp., 2.) CH3NO2, reflux; Yield given. Multistep reaction;

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + (2E)-4-[(tert-butyldiphenylsilyl)oxy]-2-fluorobut-2-enal (186953-22-0) → (7E,9E,13E)-tert-butyldiphenylsilyl 13-demethyl-13-fluororetinyl ether (186953-39-9)

Conditions	Yield
With n-butyllithium 1.) THF, hexane, -78 deg C, 2.) THF, hexane, 25 deg C, 5 h; Yield given. Multistep reaction;

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + (Z)-1-(tert-butyldimethylsilyloxy)-3-iodo-3-methylprop-2-ene (148802-00-0) → tert-butyldimethylsilyl Δ13-(Z)-retinyl ether (118304-54-4) + tert-Butyl-[(2Z,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyloxy]-dimethyl-silane (118304-54-4, 118353-70-1)

Conditions	Yield
With potassium tert-butylate; tert.-butyl lithium In diethyl ether; pentane at -75 - 25℃; for 6h; Wittig reaction;

4,4'-diapo-ψ,ψ-carotene-4,4'-dial (13920-19-9, 5056-18-8) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → 3,7,11,15,20,24,28,32-octamethyl-1,34-bis(2,6,6-trimethylcyclohex-1-enyl)tetratriaconta-1,3,5,7,9,11,13,15,17,19,21,23,25,27,29,31,33-heptadecaene (24513-48-2)

Conditions	Yield
With sodium hydride In dichloromethane Wittig reaction;	67 % Spectr.

6,6'-diapocarotene-6,6'-dial (34561-05-2) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → 3,9,13,18,22,28-hexamethyl-1,30-bis(2,6,6-trimethylcyclohex-1-enyl)triaconta-1,3,5,7,9,11,13,15,17,19,21,23,25,27,29-pentadecaene

Conditions	Yield
With sodium hydride In dichloromethane Wittig reaction;	66 % Spectr.

Upstream product

• 62285-89-6 [(2E)-3-(5,5-dimethyl-1,3-dioxan-2-yl)but-2-en-1-yl](triphenyl)phosphonium chloride 
• 62285-88-5 2-[(2E)-4-chlorobut-2-en-2-yl]-5,5-dimethyl-1,3-dioxane 
• 62285-59-0 4-CHLOROBENZALDEHYDE-2,3,5,6-D4 
• 62285-58-9 2,6-Dimethylbenzyl alcohol 
• 622-85-5 Propoxybenzene 
• 62285-43-2 {[bis(1-methylethoxy)phosphoryl](dimethoxyphosphoryl)methylidene}diazenium 
• 62285-42-1 [(diethylsulfamoyl)(dimethoxyphosphoryl)methylidene]diazenium 
• 622854-00-6 1,2-Ethanediol, 1-(4-hydroxyphenyl)-, (1S)- (9CI) 
• 6228-53-1 zinc succinate 
• 622851-30-3 Ethanone, 1,1-trans-1,4-cyclohexanediylbis- (9CI) 
• 62284-99-5 2,3,4,5-tetrabromohexanoic acid 
• 62284-92-8 2,4,8,10-Tetraoxa-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(2-phenylethyl)-, 3,9-dioxide 
• 62284-79-1 (-)-4-BROMOTETRAMISOLE OXALATE 
• 622847-32-9 2-bromomethyl-4-methyl-benzoic acid methyl ester 

Downstream Products

• 6228-62-2 Selenodiacetic acid 
• 622863-63-2 1H-Indole,2-ethenyl-5-methoxy-(9CI) 
• 62286-43-5 2-Oxepanone, polymer with N-(1,3-dimethylbutylidene) -N'-[2-[(1,3-dimethylbutylidene)amino]ethyl]-1,2 -ethanediamine, 5-isocyanato-1-(isocyanatomethyl) -1,3,3-trimethylcyclohexane and 2,2'-oxybis[ethanol] 
• 622864-47-5 3-Furoicacid,4,5-dihydro-4-oxo-,ethylester(7CI) 
• 622864-48-6 Boronic acid, (3-hydroxy-4-methoxyphenyl)- (9CI) 
• 622864-54-4 PD407824 
• 622864-56-6 5-METHOXY-1-BENZOTHIOPHENE-2-CARBALDEHYDE 
• 622865-34-3 Carbamic acid, (4-hydroxy-2,2-dimethylbutyl)-, 1,1-dimethylethyl ester (9CI) 
• 622-86-6 2-Phenoxyethyl chloride 
• 622866-04-0 ERYTHRO-N-BOC-L-4-NITROPHENYLALANINE EPOXIDE 
• 622867-52-1 tert-butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 62287-32-5 ammonium 4-[(2-{2-(1-methylethoxy)-1-[(1-methylethoxy)carbonyl]-2-oxoethylidene}-1,3-dithiolan-4-yl)oxy]-4-oxobutanoate 
• 6228-73-5 CYCLOPROPANECARBOXAMIDE 
• 62287-35-8 Lead p-aminobenzoate 

Recommend Products

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