(4S,6R)-6-(2-Benzyloxy)ethyl-4-hydroxymethyl-1,5,5-trimethylcyclohexene

Base Information

Chemical Name:(4S,6R)-6-(2-Benzyloxy)ethyl-4-hydroxymethyl-1,5,5-trimethylcyclohexene
CAS No.:107953-18-4
Molecular Formula:C₁₉H₂₈O₂
Molecular Weight:288.43
Hs Code.:

Synonyms:(4S,6R)-6-(2-Benzyloxy)ethyl-4-hydroxymethyl-1,5,5-trimethylcyclohexene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S,6R)-6-(2-Benzyloxy)ethyl-4-hydroxymethyl-1,5,5-trimethylcyclohexene

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Technology Process of (4S,6R)-6-(2-Benzyloxy)ethyl-4-hydroxymethyl-1,5,5-trimethylcyclohexene

There total 9 articles about (4S,6R)-6-(2-Benzyloxy)ethyl-4-hydroxymethyl-1,5,5-trimethylcyclohexene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.8%

: 107953-15-1,107953-16-2,138808-89-6,138808-90-9
(3aR,7S,7aS)-7-(2-Benzyloxy-ethyl)-6,7a-dimethyl-1,3,3a,4,7,7a-hexahydro-isobenzofuran-1-ol

: 107953-18-4
(4S,6R)-6-(2-Benzyloxy)ethyl-4-hydroxymethyl-1,5,5-trimethylcyclohexene

Guidance literature:: With sodium hydroxide; hydrazine hydrate; In diethylene glycol; 1) 35 min, 100 deg C, 2) to 210 deg C, 1 h, 3) 2 h, 210 deg C;
DOI:10.1248/cpb.39.2540

Reference yield:

: 138703-08-9
6-Benzyloxy-3-methyl-1,3-hexadiene

: 107953-18-4
(4S,6R)-6-(2-Benzyloxy)ethyl-4-hydroxymethyl-1,5,5-trimethylcyclohexene

Guidance literature:: Multi-step reaction with 9 steps

1: 97.2 percent / hydroquinone / benzene / 19 h / Heating

2: 1) NaHCO₃, 2) KI, I₂ / 1) water, 2 h, r.t., 2) water, 17 h, r.t.

3: 4.58 g / BH₃*Me₂S, B(OMe)3 / tetrahydrofuran / 7 h / Ambient temperature

4: 63 percent / Zn-dust, AcOH / 1 h / 90 °C

5: 1) LDA / 1) THF, -65 deg C, 30 min, 2) -65 deg C, 4 h

6: 77.4 percent / i-Bu₂AlH / tetrahydrofuran; toluene / 1 h / -65 °C

7: 20.7 percent / CSA / benzene / 0.5 h

8: 93.7 percent / TsOH / dioxane; H₂O / 1 h / Heating

9: 91.8 percent / NaOH, 80percent N₂H₄ / bis-(2-hydroxy-ethyl) ether / 1) 35 min, 100 deg C, 2) to 210 deg C, 1 h, 3) 2 h, 210 deg C

With sodium hydroxide; Trimethyl borate; dimethylsulfide borane complex; camphor-10-sulfonic acid; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; hydroquinone; potassium iodide; zinc; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; water; toluene; diethylene glycol; benzene;
DOI:10.1248/cpb.39.2540

Reference yield:

: 107953-12-8,138808-87-4
(3aR*,7S*,7aS*)-7-(2-Benzyloxy)ethyl-6-methyl-3a,4,7,7a-tetrahydrophthalide

: 107953-18-4
(4S,6R)-6-(2-Benzyloxy)ethyl-4-hydroxymethyl-1,5,5-trimethylcyclohexene

Guidance literature:: Multi-step reaction with 5 steps

1: 1) LDA / 1) THF, -65 deg C, 30 min, 2) -65 deg C, 4 h

2: 77.4 percent / i-Bu₂AlH / tetrahydrofuran; toluene / 1 h / -65 °C

3: 20.7 percent / CSA / benzene / 0.5 h

4: 93.7 percent / TsOH / dioxane; H₂O / 1 h / Heating

5: 91.8 percent / NaOH, 80percent N₂H₄ / bis-(2-hydroxy-ethyl) ether / 1) 35 min, 100 deg C, 2) to 210 deg C, 1 h, 3) 2 h, 210 deg C

With sodium hydroxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; toluene-4-sulfonic acid; hydrazine hydrate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; water; toluene; diethylene glycol; benzene;
DOI:10.1248/cpb.39.2540