Sulfuric Acid → 2,5-Bishydroxymethyl-4'-hexyloxybiphenyl

HRID 1635757Notes

Reaction equation

HRID 1635757 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:30]=[C:29]([C:31](OCC)=[O:32])[CH:28]=[CH:27][C:21]=2[C:22](OCC)=[O:23])=[CH:16][CH:15]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].S(=O)(=O)(O)O>C1COCC1>[OH:23][CH2:22][C:21]1[CH:27]=[CH:28][C:29]([CH2:31][OH:32])=[CH:30][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11069361Diethyl 2-(4'-hexyloxyphenyl)terephthalateHCID 21226445Aluminium lithium hydride

Product 1

HCID 153765802,5-Bishydroxymethyl-4'-hexyloxybiphenyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAlH4 (5.3 g, 140 mmol) and about 200 ml of THF were blanketed with argon in a reaction vessel and diethyl 2-(4′-hexyloxyphenyl)terephthalate (40 g, 100 mmol) (cf. C1) together with a further 50 ml of THF were slowly added dropwise from a dropping funnel. The reaction mixture was stirred vigorously during this addition. The mixture was subsequently refluxed for about one hour. The reaction mixture was brought to RT and, while cooling in a water bath and blanketing with argon, ice water was carefully added dropwise until gas evolution had ceased. Dilute (10% strength) sulfuric acid was subsequently added dropwise until the turbid gray mixture was clear. The phases were separated by addition of chloroform and the aqueous phase was shaken twice with chloroform. The organic phases were washed once with H2O and subsequently evaporated. The crude product obtained was recrystallized from hexanelethyl acetate (5:1).

Workup

  1. temperatureThe mixture was subsequently refluxed for about one hour
  2. customwas brought to RT
  3. temperaturewhile cooling in a water bath
  4. additionwas carefully added dropwise until gas evolution
  5. additionwas subsequently added dropwise until the turbid gray mixture
  6. customThe phases were separated by addition of chloroform
  7. stirringthe aqueous phase was shaken twice with chloroform
  8. washThe organic phases were washed once with H2O
  9. customsubsequently evaporated

Sources & evidence

ORD record
ord-b2047d0a6719455f8d39f22d6af8a163
Source dataset
uspto-grants-2003_01
Patent number
US06509507B2

Reaction notes

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