Methanol → 2-(Phenylmethoxy)-3-(4-tetradecylphenoxy)-1-propanol

HRID 235720Notes

Reaction equation

HRID 235720 reaction equation
[C:1]1([CH2:7][O:8][CH:9]([CH2:32][O:33]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[C:1]1([CH2:7][O:8][CH:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:14][CH:13]=2)[CH2:32][OH:33])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 202183791-[2-(Phenylmethoxy)-3-(triphenylmethoxy)propoxy]-4-tetradecylbenzene

Product 1

HCID 202184432-(Phenylmethoxy)-3-(4-tetradecylphenoxy)-1-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An about 14.6 g portion of 1-[2-(phenylmethoxy)-3-(triphenylmethoxy)propoxy]-4-tetradecylbenzene was dissolved in about 50 ml of tetrahydrofuran. To this solution was added about 50 ml of methanol and about 100 mg of p-toluenesulfonic acid. The mixture was stirred under argon for several hours and the solvents were then removed. The residue was dissolved in ether, washed with aqueous sodium bicarbonate, dried and the ether evaporated. The residue was purified by chromatography on silica gel, eluting with hexane:ether (about 12:1), giving about 7.6 g of the desired title compound, mp 50°-51° C.

Workup

  1. customthe solvents were then removed
  2. dissolutionThe residue was dissolved in ether
  3. washwashed with aqueous sodium bicarbonate
  4. customdried
  5. customthe ether evaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with hexane

Sources & evidence

ORD record
ord-c9500d67b6864d45837846f6d6a5bffb
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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