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

HRID 990174Notes

Reaction equation

HRID 990174 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) was added to about 200 ml of THF under a blanket of argon and diethyl 2-(4′-hexyloxyphenyl)terephthalate (40 9, 100 mmol) (cf. C1) together with a further 50 ml of THF was slowly added dropwise from a dropping funnel. The reaction mixture was vigorously stirred during this addition. It was subsequently refluxed for about one hour. The reaction mixture was brought to RT and, with water bath cooling and under a blanket of 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 with chloroform (twice). The organic phases were washed once with H2O and subsequently evaporated. The resulting crude product was recrystallized from hexane/ethyl acetate (5/1).

Workup

  1. additionwas slowly added dropwise from a dropping funnel
  2. temperatureIt was subsequently refluxed for about one hour
  3. customThe reaction mixture was brought to RT and, with 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 with chloroform (twice)
  8. washThe organic phases were washed once with H2O
  9. customsubsequently evaporated
  10. customThe resulting crude product was recrystallized from hexane/ethyl acetate (5/1)

Sources & evidence

ORD record
ord-7d1e84bb2f3f469d9418ede3451b387b
Source dataset
uspto-grants-2002_10
Patent number
US06458909B1

Reaction notes

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