Water → HCID 14257790, compound

HRID 868433Notes

Reaction equation

HRID 868433 reaction equation
I[CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.[OH:13][CH:14]([C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[Na+].O>CS(C)=O.C1COCC1>[OH:13][CH:14]([C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 27630372-(Iodomethyl)-1,2,3,4-tetrahydronaphthaleneHCID 117900843-(1-Hydroxyhexyl)phenol

Product 1

HCID 14257790HCID 14257790, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.0 g (0.018 mol) 2-(iodomethyl)-1,2,3,4-tetrahydronaphthalene, 3.4 g (0.018 mol) 3-(1-hydroxyhexyl)phenol and 3.4 ml NaOH (5N) in 50 ml DMSO and 20 ml THF was stirred at room temperature for a period of 48 hours. The reaction mixture was concentrated under reduced pressure. The concentrated reaction mixture was poured into water and extracted with ether. The ether extract was washed with water, dried over MgSO4 and concentrated to dryness under reduced pressure. The residue was passed through a silica gel comumn using hexane/ethyl acetate (3:1) as eluent. Evaporation of eluent gave an oily product (1.3 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe concentrated reaction mixture
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness under reduced pressure
  8. customEvaporation of eluent

Sources & evidence

ORD record
ord-5404180083674ffb8296e1910527dae7
Source dataset
uspto-grants-1988_10
Patent number
US04778931

Reaction notes

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