HCID 86707584, compound → HCID 86707583, compound

HRID 2279974Notes

Reaction equation

HRID 2279974 reaction equation
COCCOC[O:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29]CC4C=CC=CC=4)=[CH:25][CH:24]=3)[CH:20]=[C:19]([C:37]3[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][CH2:45][O:46]COCCOC)=[CH:39][CH:38]=3)[CH:18]=2)=[CH:13][CH:12]=1>C1COCC1>[OH:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:18]=[C:19]([C:37]3[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][CH2:45][OH:46])=[CH:39][CH:38]=3)[CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[CH:22]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 1

HCID 86707584HCID 86707584, compound

Product 1

HCID 86707583HCID 86707583, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.50 g (3.55 mmol) 4,4″-bis-[3-(2-methoxy-ethoxymethoxy)-propyl]-5′-(4-benzyloxyphenyl)-[1,1′;3′,1″]terphenyl are hydrogenated in 70 ml THF on Pd/activated charcoal until the reaction is completed. The catalyst is filtered off, the solvent is removed in vacuo, the residue is dissolved in 20 ml THF, 5 ml 25% hydrochloric acid are added dropwise under cooling and the mixture is stirred overnight at RT. After addition of 100 ml MTB ether the solution is washed with water and sat. aq. sodium chloride solution and dried over sodium sulfate. The solvent is removed in vacuo and the residue is filtered through silica gel with dichloromethane/MTB ether (9:1), to give 3-[4″-(3-hydroxy-propyl)-5′-(4-hydroxyphenyl)-[1,1′;3′,1″]terphenyl-4-yl]-propane-1-ol as colourless oil.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in 20 ml THF
  4. addition5 ml 25% hydrochloric acid are added dropwise
  5. temperatureunder cooling
  6. additionAfter addition of 100 ml MTB ether the solution
  7. washis washed with water and sat. aq. sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. customThe solvent is removed in vacuo
  10. filtrationthe residue is filtered through silica gel with dichloromethane/MTB ether (9:1)

Sources & evidence

ORD record
ord-9f5859b3e76f463bb8c1c0dcc6b59263
Source dataset
uspto-grants-2015_09
Patent number
US09133395B2

Reaction notes

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