824-94-2

Basic information

• Product Name: 4-Methoxybenzylchloride
• Synonyms: P-METHOXYBENZYL CHLORIDE;alpha-Chloro-4-methoxytoluene;Anisole, p-(chloromethyl)-;Benzene, 1-(chloromethyl)-4-methoxy-;p-(Chloromethyl)anisole;p-Anisyl chloride;METHOXYBENZYLCHLORIDE(P-);1-CHLOROMETHYL-4-METHOXYBENZENE
• CAS NO: 824-94-2
• Molecular Formula: C₈H₉ClO
• Molecular Weight: 156.61
• EINECS: 212-540-6
• Product Categories: Biochemistry;Reagents for Oligosaccharide Synthesis;alkyl chloride
• Mol File: 824-94-2.mol
• Article Data: 127

Chemical Properties

• Melting Point: −1 °C(lit.)
• Boiling Point: 117-118 °C14 mm Hg(lit.)
• Flash Point: 229 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.155 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0495mmHg at 25°C
• Refractive Index: n20/D 1.548(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: slowly decomposes
• CAS DataBase Reference: 4-Methoxybenzylchloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxybenzylchloride(824-94-2)
• EPA Substance Registry System: 4-Methoxybenzylchloride(824-94-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• F: 10-19-21
• TSCA: No
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 824-94-2(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

O/N protecting group reagent which can be mildly oxidatively cleaved, e.g., with ceric ammonium nitrate.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 20, p. 190, 1977 DOI: 10.1021/jm00212a002The Journal of Organic Chemistry, 53, p. 3634, 1988 DOI: 10.1021/jo00250a048

General Description

4-Methoxybenzyl chloride undergoes mild oxidative claevage with ceric ammonium nitrate.

Purification Methods

Purify 4-anisyl chloride by fractional distillation under vacuum, and the middle fraction is redistilled at 10-6 mm at room temperature by intermittent cooling of the receiver in liquid N2, and the middle fraction is collected. [Mohammed & Kosower J Am Chem Soc 93 2709 1971, Beilstein 6 IV 2137.]

InChI:InChI=1/C8H9ClO/c1-10-8-4-2-7(6-9)3-5-8/h2-5H,6H2,1H3

Synthetic route

4-Methoxybenzyl alcohol (105-13-5) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane at 20℃; Substitution;	100%
With thionyl chloride; triethylamine In dichloromethane at -10 - 0℃; for 4.25h; Large scale;	99%
With oxalyl dichloride; 1-methyl-3-(2-(3-methyl-2-oxoimidazolidin-1-yl)ethyl)-1H-imidazol-3-ium hexafluorophosphate at 20 - 60℃; for 24h; Reagent/catalyst;	99%

1-methoxy-4-((methylsulfinyl)methyl)benzene (15733-09-2) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With hydrogenchloride In tetrachloromethane for 0.25h; Heating;	100%

1-methoxy-4-((methylsulfinyl)methyl)benzene (15733-09-2) + HCl gas → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
In tetrachloromethane for 15h; Heating;	100%

Methyl-thiocarbamic acid S-(4-methoxy-benzyl) ester (27979-81-3) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With hydrogenchloride; N-chloro-succinimide In acetonitrile at 10℃;	98%

p-methoxybenzylmercuric chloride (34820-80-9) → p-methoxybenzyl chloride (824-94-2) + mercury

Conditions	Yield
In nitromethane byproducts: Hg2Cl2; vacuum-sealed ampule, 65°C for 50h; separation of Hg, analysis of decanted soln. by TLC and GLC;	A 90% B 97%

trimethyl(4-methoxybenzyloxy)silane (14629-56-2) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With 4-aminophenyl diphenylphosphinite; N-chloro-succinimide In dichloromethane for 1h; Heating;	96%

2-(4-methoxy-benzyloxy)-tetrahydro-pyran (18494-82-1) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With 4-aminophenyl diphenylphosphinite; N-chloro-succinimide In dichloromethane for 1.5h; Heating;	95%

p-methoxybenzylmercuric chloride (34820-80-9) → p-methoxybenzyl chloride (824-94-2) + mercury

Conditions	Yield
In nitromethane at 65℃; for 50h;	A 90% B n/a

4,4'-dimethoxydibenzyl ether (5405-95-8) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With tetrachlorosilane; NbCl3(N,N′-bis-(2,6-diisopropylphenyl)-1,4-diaza-2,3-dimethyl-1,3-butadiene) In chloroform-d1 at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;	85%

Bromotrichloromethane (75-62-7) + 4-Methoxybenzyl alcohol (105-13-5) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
Stage #1: Bromotrichloromethane With triphenylphosphine In dichloromethane at 20℃; for 0.666667h; Appel reaction; in air; Stage #2: 4-Methoxybenzyl alcohol In dichloromethane at 20℃; Appel reaction; in air;	84%

methanol (67-56-1) + 4-Methoxybenzyl alcohol (105-13-5) → 1-methoxy-4-(methoxymethyl)benzene (1515-81-7) + p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
Stage #1: 4-Methoxybenzyl alcohol With titanium tetrachloride In chloroform at 20℃; for 0.0166667h; Molecular sieve; Stage #2: methanol In chloroform for 9h; Reflux;	A 82% B 10%
Stage #1: 4-Methoxybenzyl alcohol With titanium tetrachloride In chloroform at 20℃; for 0.0166667h; Molecular sieve; Stage #2: methanol In chloroform for 1h; Reflux;	A 5% B 12%

cyclohexyl(4-methoxybenzyl)sulfane (93394-70-8) → 1,2-dicyclohexyl disulfide (2550-40-5) + 4-methoxy-benzaldehyde (123-11-5) + p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With 2,6-dimethylpyridine; tris-(4-bromophenyl)aminium hexachloroantimonate In dichloromethane; acetonitrile for 1h; Mechanism;	A 80% B n/a C 80%

formaldehyd (50-00-0) + methoxybenzene (100-66-3) → 1-methoxy-2,4-bis(chloromethyl)benzene (25445-34-5) + p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With hydrogenchloride; 1-ethyl-3-methylimidazolium hexafluorophosphate at 70℃; for 5h; Ionic liquid;	A 79% B 16%
With hydrogenchloride; 1-ethyl-3-methylimidazolium tetrafluoroborate at 70℃; for 5h;	A 76% B 17%

benzoyl chloride (98-88-4) + 4-Methoxybenzyl alcohol (105-13-5) → p-methoxybenzyl benzoate (24318-41-0) + p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With racemic methyl phenyl sulfoxide In acetonitrile at 0 - 20℃; for 14.25h; Sealed tube;	A n/a B 78%
In tert-butyl methyl ether at 20℃; for 24h;	A n/a B 32 %Spectr.

S-(4-methoxybenzyl) ethanethioate (102607-00-1) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With hydrogenchloride; N-chloro-succinimide In acetonitrile at 10℃;	74%

4-methoxy-benzaldehyde (123-11-5) → 4,4'-dimethoxydibenzyl ether (5405-95-8) + p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With chloro-trimethyl-silane; thionyl chloride; 1,1,3,3-Tetramethyldisiloxane; zinc(II) iodide at -70℃; for 2.5h;	A 40% B 60%

4-Methoxybenzyl alcohol (105-13-5) → 4-methoxy-benzaldehyde (123-11-5) + p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With N-chloro-succinimide; N-(phenylthio)-N-(tert-butyl)amine; potassium carbonate; 4 A molecular sieve In dichloromethane at 0℃; for 1h;	A 29% B 60%

4-methoxy-benzaldehyde (123-11-5) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With dichloromethylsilane; iron(III) chloride In 1,2-dimethoxyethane for 4h; Heating;	55%
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 2: thionyl chloride / dichloromethane / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: thionyl chloride / Inert atmosphere View Scheme

bis(trichloromethyl) carbonate (32315-10-9) + 1-(phenylmethyl)-4-[(4'-methoxyphenyl)methyl]piperazine (148120-38-1) → 4-(phenylmethyl)-1-piperazine carbonyl chloride (63763-66-6) + p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
In dichloromethane	A 53% B n/a

ethanol (64-17-5) + (4-methoxy-benzyl)-trimethyl-silane (17988-20-4) → 1-ethoxymethyl-4-methoxybenzene (55249-73-5) + 4-methoxy-benzaldehyde (123-11-5) + p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With oxovanadium(V) ethoxydichloride; oxygen at 20℃; for 6h;	A 51% B 40% C 5%

4-methoxybenzyltri-n-butylstannane (74260-40-5) → 4-methoxy-benzaldehyde (123-11-5) + p-methoxybenzyl chloride (824-94-2) + 4-Methoxybenzyl alcohol (105-13-5)

Conditions	Yield
With C2H2Cl2F3O2V; oxygen In tert-butyl alcohol at 20℃; for 2h;	A 48% B 38% C 14%

(4-methoxy-benzyl)-trimethyl-silane (17988-20-4) + isopropyl alcohol (67-63-0) → 1-methoxy-4-[(propan-2-yloxy)methyl]benzene (98446-83-4) + 4-methoxy-benzaldehyde (123-11-5) + p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With oxovanadium(V) ethoxydichloride; oxygen at 0℃; for 24h;	A 8% B 44% C 4%

bis(trichloromethyl) carbonate (32315-10-9) + 4-methoxy-N-methyl-N-phenylbenzenemethanamine (37931-52-5) → N-phenyl-N-methylcarbamoyl chloride (4285-42-1) + p-methoxybenzyl chloride (824-94-2) + C16H17ClNO2(1+)*Cl(1-)

Conditions	Yield
for 0.5h;	A 44% B n/a C n/a

4-methoxybenzyl iodide (70887-29-5) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With FeCl2(phen)3 In acetonitrile at 60℃; for 0.5h;	34%
With pyridine; tributyltin chloride at 50℃; Thermodynamic data; Equilibrium constant; Δ G;	27 % Spectr.

(4-Methoxy-benzyl)-phosphonic acid isopropyl ester 2-thioxo-2H-pyridin-1-yl ester (117309-25-8) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With tetrachloromethane; 2,2'-azobis(isobutyronitrile) In benzene Heating;	27%

(4-Methoxybenzyl)trimethylstannane (51755-57-8) → 1,2-bis(4-methoxyphenyl)ethane (1657-55-2) + 4-methoxy-benzaldehyde (123-11-5) + p-methoxybenzyl chloride (824-94-2) + 4-Methoxybenzyl alcohol (105-13-5)

Conditions	Yield
With iodosylbenzene; (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride In benzene at 25℃; for 3h;	A 5% B 16% C 3% D 13%
With iodosylbenzene; (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride In dichloromethane at 25℃; for 3h;	A 4% B 12% C 8% D 11%

4-methoxybenzyltri-n-butylstannane (74260-40-5) → 1,2-bis(4-methoxyphenyl)ethane (1657-55-2) + 4-methoxy-benzaldehyde (123-11-5) + p-methoxybenzyl chloride (824-94-2) + 4-Methoxybenzyl alcohol (105-13-5)

Conditions	Yield
With iodosylbenzene; (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride In methanol; dichloromethane; water at 25℃; for 3h;	A 5% B 16% C 6% D 11%

4-Methylanisole (104-93-8) → p-methoxybenzyl chloride (824-94-2)

Conditions	Yield
With chlorine Einwirkung von Sonnenlicht;

chloromethyl methyl ether (107-30-2) + methoxybenzene (100-66-3) → p-methoxybenzyl chloride (824-94-2)

p-methoxybenzyl chloride (824-94-2) → 1-(azidomethyl)-4-methoxybenzene (70978-37-9)

Conditions	Yield
With sodium azide In tetrahydrofuran Inert atmosphere;	100%
With sodium azide In N,N-dimethyl-formamide at 70℃;	100%
With sodium azide In N,N-dimethyl-formamide at 65℃; for 4h;	100%

p-methoxybenzyl chloride (824-94-2) → 4-methoxybenzyl nitrate (79929-17-2)

Conditions	Yield
With silver nitrate In acetonitrile for 0.166667h;	100%
With diethyl ether; silver nitrate; calcium carbonate
Multi-step reaction with 2 steps 1: 83 percent / potassium carbonate / acetone / 5 h / Heating 2: cerium(IV) ammonium nitrate / acetonitrile View Scheme

piperidin-2-one (675-20-7) + p-methoxybenzyl chloride (824-94-2) → N-(4-Methoxybenzyl)-δ-valerolactam (128773-73-9)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Reflux; Inert atmosphere;	100%
With sodium hydride In tetrahydrofuran for 23h; Heating;	94%
With sodium t-butanolate In dimethyl sulfoxide at 20℃; for 3h;	78%
With potassium hydroxide; tetrabutylammomium bromide In toluene for 8h; Heating;	52%
With tetrabutylammomium bromide; potassium hydroxide In toluene for 8h; Dean-Stark;	28.8 g

2,4,5-tribromo-1H-imidazole (2034-22-2) + p-methoxybenzyl chloride (824-94-2) → 2,4,5-tribromo-1-(4-methoxybenzyl)-1H-imidazole (101901-58-0)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 55℃; for 18h;	100%
With sodium carbonate In N,N-dimethyl-formamide Heating;	90%
With sodium carbonate In N,N-dimethyl-formamide	90%
Stage #1: 2,4,5-tribromo-1H-imidazole With sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In tetrahydrofuran for 6h; Inert atmosphere; Reflux;	53%

tert-butylamine (75-64-9) + p-methoxybenzyl chloride (824-94-2) → N-(p-methoxybenzyl)-N-tert-butylamine (22675-83-8)

Conditions	Yield
	100%
With sodium carbonate; sodium iodide In N,N-dimethyl-formamide at 65℃; for 4h; Inert atmosphere;	56%
In N,N-dimethyl-formamide for 6h; Yield given;

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (329899-64-1) + p-methoxybenzyl chloride (824-94-2) → (3aR,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (329899-60-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran; dimethyl sulfoxide Ambient temperature;	100%

(2R,3S,4R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-[1,3]dithian-2-yl-pentan-3-ol (114114-36-2) + p-methoxybenzyl chloride (824-94-2) → (S)-4-[(1R,2S,3R)-3-[1,3]Dithian-2-yl-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolane (114130-12-0)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	100%
With sodium hydride In N,N-dimethyl-formamide for 1h;	87%
With sodium hydride 1.) DMF, room temp., 5 min, 2.) DMF, 1 h; Yield given. Multistep reaction;

(Z)-1-acetyl-6-(2,4,5-trimethoxy-3-methylphenylmethyl)-3-(2,4,5-trimethoxy-3-methylphenylmethylene)-2,5-piperazinedione (113296-75-6) + p-methoxybenzyl chloride (824-94-2) → 1-Acetyl-4-(4-methoxy-benzyl)-6-(2,4,5-trimethoxy-3-methyl-benzyl)-3-[1-(2,4,5-trimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 25℃; for 2h;	100%
With sodium hydride 1.) DMF, 0 deg C, 30 min, 2.) DMF, 25 deg C, 2 h; Multistep reaction;

1-(3-chloro-4-methoxybenzyl)-4-chloro-1,2,3-triazole + p-methoxybenzyl chloride (824-94-2) → 5-Chloro-3-(3-chloro-4-methoxy-benzyl)-1-(4-methoxy-benzyl)-3H-[1,2,3]triazol-1-ium; chloride

Conditions	Yield
	100%

1-benzyl-4-chloro-1,2,3-triazole (116932-57-1) + p-methoxybenzyl chloride (824-94-2) → 3-Benzyl-5-chloro-1-(4-methoxy-benzyl)-3H-[1,2,3]triazol-1-ium; chloride

Conditions	Yield
	100%

p-methoxybenzyl chloride (824-94-2) → 4-methoxybenzyl iodide (70887-29-5)

Conditions	Yield
With sodium iodide In acetone at 20℃; for 1.5h;	100%
With sodium iodide In acetone for 16h; Ambient temperature;	91%
With sodium iodide In acetone at 25℃; for 16h; Darkness;	85%

p-methoxybenzyl chloride (824-94-2) → 4-methoxy-benzaldehyde (123-11-5)

Conditions	Yield
With water; sodium hydroxide at 20℃; for 0.05h; Microwave irradiation;	100%
hydrotalcite In dimethyl sulfoxide at 140℃; for 1.5h; Kornblum reaction;	96%
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 1.5h;	95%

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6) + p-methoxybenzyl chloride (824-94-2) → (S)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane (109786-73-4)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	100%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	100%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	100%

p-methoxybenzyl chloride (824-94-2) + 2-imidazolecarbaldehyde (10111-08-7) → 1-(4-methoxybenzyl)-1H-imidazole-2-carbaldehyde (95460-12-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	100%
With tetrabutylammomium bromide; potassium carbonate at 120℃; for 2h;	34%

p-methoxybenzyl chloride (824-94-2) → (3S,3aR,6aS)-6-Benzyloxymethyl-3-(4-methoxy-benzyloxymethyl)-hexahydro-1,2,4-trioxa-6-aza-cyclopropa[e]inden-5-one

Conditions	Yield
With 3,3-dimethyldioxirane In dichloromethane at 0℃;	100%

p-methoxybenzyl chloride (824-94-2) + (4E,6E)-2,4,6-trimethyl-1,4,6-nonatrien-3-ol → (4E,6E)-3-(p-methoxybenzyloxy)-2,4,6-trimethyl-1,4,6-nonatriene

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 3h;	100%

1 ,5-pentanediol (111-29-5) + p-methoxybenzyl chloride (824-94-2) → 5-(4-methoxybenzyloxy)-1-pentanol (131375-63-8)

Conditions	Yield
Stage #1: 1 ,5-pentanediol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 3h; Inert atmosphere; Reflux; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 20℃; for 12h; Inert atmosphere; Reflux;	100%
Stage #1: 1 ,5-pentanediol With sodium hydride In tetrahydrofuran for 3h; Heating; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran for 15h;	99%
Stage #1: 1 ,5-pentanediol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 4.5h; Reflux; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil for 17h; Reflux;	97%

p-methoxybenzyl chloride (824-94-2) + 5-bromo-2H-isoquinolin-1-one (190777-77-6) → 5-bromo-2-(4-methoxyphenylmethyl)isoquinoline-1(2H)-one

Conditions	Yield
With sodium iodide; lithium hexamethyldisilazane In tetrahydrofuran 1.) 2 h, 2.) 5 d;	100%

p-methoxybenzyl chloride (824-94-2) + tert-butyl (3,5-dibromophenyl)carbamate (195134-70-4) → 3,5-dibromo-N-(tert-butoxycarbonyl)-N-(4-methoxybenzyl)aniline (195134-80-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1.) 20 min, 2.) 21 h;	100%

N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide (143571-61-3) + p-methoxybenzyl chloride (824-94-2) → N-[(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1.) 0 deg C, 20 min, 2.) room temperature, 10 h;	100%

p-methoxybenzyl chloride (824-94-2) + 2-[(4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol (199792-19-3) → (4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-6-[2-(4-methoxy-benzyloxy)-ethyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (199792-20-6)

Conditions	Yield
With potassium hydride In tetrahydrofuran for 3h; Ambient temperature;	100%
With tetra-(n-butyl)ammonium iodide; potassium hydride In tetrahydrofuran for 3h; Ambient temperature; Yield given;

1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol (67320-20-1, 83692-41-5, 94292-91-8, 64722-95-8) + p-methoxybenzyl chloride (824-94-2) → (1'S,4R)-4-(3',3'-bisethylthio-1'-p-methoxybenzyloxypropyl)-2,2-dimethyl-1,3-dioxolane (152453-71-9)

Conditions	Yield
With sodium hydride; dimethyl sulfoxide for 4h; Ambient temperature;	100%
With sodium hydride In N,N-dimethyl-formamide	100%
With sodium hydride In N,N-dimethyl-formamide for 2h;	100%
Stage #1: 1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol With sodium hydride In DMF (N,N-dimethyl-formamide) for 0.5h; Stage #2: p-methoxybenzyl chloride In DMF (N,N-dimethyl-formamide) at 20℃; for 4h;

p-methoxybenzyl chloride (824-94-2) + 3-hydroxy-2-methyl-1-propene (513-42-8) → 1-((methallyloxy)methyl)-4-methoxybenzene (189366-67-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃;	100%
With sodium hydroxide 1.) THF, mineral oil, DMF, 0 deg C, 30 min; 2.) THF, 2 h;	97%
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; 1.) 30 min, 2.) 2 h;

Succinimide (123-56-8) + p-methoxybenzyl chloride (824-94-2) → 1-[(4-methoxyphenyl)methyl]-2,5-pyrrolidinedione (108640-66-0)

Conditions	Yield
With potassium carbonate In acetonitrile	100%
With potassium carbonate In acetonitrile at 25℃; for 16h;
With potassium carbonate In acetonitrile at 25℃; for 16h;
With potassium carbonate In acetonitrile at 25℃; for 16h;

p-methoxybenzyl chloride (824-94-2) + methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside (72904-78-0) → methyl 4,6-O-benzylidene-3-deoxy-2-O-(4-methoxybenzyl)-α-D-arabinopyranoside (226885-87-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃;	100%
With sodium hydride 1) DMF, 0 deg C, 30 min; 2) DMF, 0 deg C, 3 h; Yield given; Multistep reaction;

p-methoxybenzyl chloride (824-94-2) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → 4-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane (156147-59-0)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 20h;	100%
Stage #1: (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: p-methoxybenzyl chloride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 20℃;	100%
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere; Reflux;	89%

p-methoxybenzyl chloride (824-94-2) + (+/-)-1,4,5-tri-O-allyl-2,3-O-cyclohexylidene-myo-inositol → (+/-)-1,4,5-tri-O-allyl-2,3-O-cyclohexylidene-6-O-p-methoxybenzyl-myo-inositol

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; Arylation;	100%

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 100-66-3 methoxybenzene 
• 5405-95-8 4,4'-dimethoxydibenzyl ether 
• 98-88-4 benzoyl chloride 
• 105-13-5 4-Methoxybenzyl alcohol 
• 75-36-5 acetyl chloride 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 99-96-7 4-hydroxy-benzoic acid 
• 75-62-7 Bromotrichloromethane 
• 67-56-1 methanol 
• 14289-62-4 1-(allyloxymethyl)-4-methoxybenzene 
• 34820-80-9 p-methoxybenzylmercuric chloride 
• 612-16-8 (2-methoxyphenyl)methanol 
• 100-09-4 4-methoxybenzoic acid 

Downstream Products

• 64834-63-5 2-[(4-methoxybenzyl)amino]ethanol 
• 109599-83-9 (2-chloro-ethyl)-bis-(4-methoxy-benzyl)-amine 
• 726-18-1 4,4'-dianisylmethane 
• 145162-51-2 1-(p-methoxyphenyl)methyl-pyrazole 
• 140-69-2 4-methoxybenzylhydrazine 
• 55249-73-5 1-ethoxymethyl-4-methoxybenzene 
• 104-47-2 p-methoxybenzylnitrile 
• 1515-81-7 1-methoxy-4-(methoxymethyl)benzene 
• 17061-62-0 N,N-bis(p-methoxybenzyl)amine 
• 2393-23-9 4-methoxy-benzylamine 
• 6258-60-2 p-methoxybenzylmercaptan 
• 79929-17-2 4-methoxybenzyl nitrate 
• 70978-37-9 1-(azidomethyl)-4-methoxybenzene 
• 82101-69-7 1-methoxy-4-(methyl-d) benzene 

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