Methanol → HCID 9820463, compound

HRID 1003636Notes

Reaction equation

HRID 1003636 reaction equation
[C:1]([C:5]1[C:10](=[O:11])[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:7](=[CH:16][C:17]#[C:18][C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.CO.[BH4-].[Na+]>O>[C:12]([C:9]1[CH:8]=[C:7]([CH2:16][C:17]#[C:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=2)[CH:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 15389066HCID 15389066, compound

Product 1

HCID 9820463HCID 9820463, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

756 mg (2 mmol) of 4-[3-(3,5-di-tert-butyl-4oxo-2,5-cyclohexadien-1-ylidene)-1-propynyl]benzoic acid and 50 ml of a mixture (50/50) of THF and methanol are introduced into a three-necked flask. 152 mg (4 mmol) of sodium borohydride are added at 0° C. and the mixture is allowed to return to room temperature. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is triturated from refluxing heptane, filtered and dried. 510 mg (64%) of 4-[3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-propynyl]benzoic acid are collected, with a melting point of 198-9° C.

Workup

  1. customto return to room temperature
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis triturated
  8. temperaturefrom refluxing heptane
  9. filtrationfiltered
  10. customdried
  11. custom510 mg (64%) of 4-[3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-propynyl]benzoic acid are collected, with a melting point of 198-9° C.

Sources & evidence

ORD record
ord-ca232423931641b7aa922dc119d4082e
Source dataset
uspto-grants-2000_04
Patent number
US06046220

Reaction notes

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