4-Bromophenetole → HCID 22145307, compound

HRID 1734963Notes

Reaction equation

HRID 1734963 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)O[CH2:2]1.C([O:14][C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1)C>>[CH2:1]([O:11][C:4]1[CH:5]=[CH:6][C:7]([CH:18]2[CH2:19][CH2:20][C:15](=[O:14])[CH2:16][CH2:17]2)=[CH:8][CH:9]=1)[CH3:2]

Participants

3

Reactant 2

HCID 685234-BromophenetoleHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 22145307HCID 22145307, compound

Procedure

Cyclohexane-1,4-dione monoethyleneacetal is reacted with a Grignard reagent prepared from 1-ethoxy-4-bromobenzene, and the product is dehydrated and then hydrogenated in the same manner as in process A (if desired, ethyleneacetal is re-introduced). The acetal moiety is removed to obtain 4-(4-ethoxyphenyl)cyclohexanone, which is then deuterated in the same manner as in process A to obtain 4-(4-ethoxyphenyl)cyclohexanone-2,2,6,6-d4. The deuterated compound is reacted with a Grignard reagent prepared from propyl bromide, and the product is dehydrated and hydrogenated. The cis-compound is separated to obtain 1-(trans-4-propylcyclohexyl-3,3,5-d3)-4-ethoxybenzene. ##STR61##

Workup

  1. customThe acetal moiety is removed

Sources & evidence

ORD record
ord-2528962c0bef4637b7962c502b911b0e
Source dataset
uspto-grants-1996_07
Patent number
US05536443

Reaction notes

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