Methanol → Methyl 4,4-bis(4-hydroxyphenyl)pentanoate

HRID 482357Notes

Reaction equation

HRID 482357 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)([CH3:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[CH3:22]O>>[CH3:22][O:12][C:11](=[O:13])[CH2:10][CH2:9][C:8]([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH3:14]

Participants

3

Reactant 2

HCID 887MethanolHCID 671744,4-Bis(4-hydroxyphenyl)valeric acid

Product 1

HCID 247957Methyl 4,4-bis(4-hydroxyphenyl)pentanoate

Procedure

To a solution in methanol (120 mL) of 4,4-bis(4-hydroxyphenyl)pentanoic acid (Aldrich Chemical Co., 12 g, 42 mmol) was added concentrated H2 SO4 (0.5 mL) and the mixture was heated to reflux for 3 hours. After cooling to room temperature the mixture was concentrated in vacuo and dissolved in ether (300 mL). The organic layer was washed with saturated aqueous NaHCO3 (2×150 mL) and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide a thick oil which was crystallized from ether/hexane to give 4,4-bis(4-hydroxyphenyl)pentanoic acid methyl ester as an off-white color solid (11.8 g, 94%), mp 130° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationwas concentrated in vacuo
  4. dissolutiondissolved in ether (300 mL)
  5. washThe organic layer was washed with saturated aqueous NaHCO3 (2×150 mL) and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto provide a thick oil which
  10. customwas crystallized from ether/hexane

Sources & evidence

ORD record
ord-e1bf653646e44eb09ed595c0775f24b6
Source dataset
uspto-grants-1998_08
Patent number
US05795900

Reaction notes

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